Distributable Net Income and Income in Respect of a Decedent

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In general, any distribution of income or principal by an estate will cause the beneficiary to be taxed to the extent of the lesser of (i) the estate’s “distributable net income” (DNI) or (ii) the amount of the distribution. Estate income is said to be “carried out” to the beneficiary. Capital gains are an exception. Since they are allocated to corpus and are not distributed to beneficiaries currently, they are generally excluded from DNI.

Two other important exceptions to the general rule for carrying out DNI exist. First, payment of specific bequests, i.e., a specific sum of money or specific property, provided they are ascertainable under the terms of the will, will not carry out fiduciary income to beneficiaries. Thus, property distributed in cash or in kind to a beneficiary will not trigger a distribution deduction at the estate level or generate gross income at the beneficiary level.

The second exception is termed the “separate share rule.” To qualify, the governing instruments must require that distributions to beneficiaries be made in “substantially the same manner as if separate trusts had been created.” Treas. Reg. §1.663(c)-3(a). The rule is intended to prevent one beneficiary from being taxed on income which was accumulated for another beneficiary, but was distributed to the first beneficiary.

To illustrate, assume that DNI equals 10, and the estate makes a distribution of 6 to one of two equal beneficiaries during the year, but makes no distribution to the other beneficiary. Without the separate share rule, the beneficiary receiving  6 would be taxable on 6, since 6 is the lesser of DNI (10) and the amount distributed (6). However, under the separate share rule, the beneficiaries would be treated as having separate equal shares of the trust. Thus, each separate “trust” would have DNI of 5. Thus, the beneficiary receiving a distribution of 6 would be taxed on 5 and would receive a principal distribution of 1.  The separate share rule does not create a “flow through” system of taxation. The beneficiary receiving no distribution would not be taxed. Rather, the remaining 5 of income would taxed to the estate.

[Note: When considering the concept of DNI, one should distinguish IRC §102, which provides that gross income does not include the value of property acquired by gift or inheritance. Therefore, if a decedent died seized only of raw land in Nebraska generating no income, and that land were deeded to his daughters, there would be no DNI and no income tax would be imposed on the daughters by reason of the bequest. On the other hand, if the land were leased, income therefrom would generate DNI, which would be taxed either to the estate, or to the daughters, if distributed to them.]

Since most decedents utilized the cash method, IRC §691 provides that income earned by the decedent before death, but collected after death, must be reported by the decedent’s estate. Such income is termed “income in respect of a decedent” or IRD. IRD items typically include (i) interest; (ii) salary or commissions earned; (iii) dividends whose record date preceded death; or (iv) gain portions of collections on a pre-death installment sale.

IRC §2033 provides that a decedent’s gross estate equals the value of all property to the extent of the decedent’s interest at the time of death. Since IRD is an “interest” of the decedent at his time of death, IRD is taxed under the transfer tax system and the income tax system. To mitigate the harshness of this result, IRC §691(c) provides a federal income tax deduction equal to the difference between the actual estate tax payable and the estate tax that would have been payable had the IRD been excluded from the gross estate.

IRC §691(b) permits deductions in respect of a decedent (DRD). Such deductions include trade or business expenses, interest, taxes, depletion, etc., which accrued before death but were not paid before death, and thus were not deductible on the decedent’s final income tax return. Since these items constitute debts, they may be deductible on the the decedent’s estate tax return, thus producing a double benefit.

Note that IRD items, in contrast to most other items included in the gross estate, do not receive a basis step up at the decedent’s death. IRC §1014(c). This can be particularly disadvantageous if the decedent sold highly appreciated property immediately before death using the installment method to report gain. In this case, the gross profit ratio would remain high. Had the contract been entered into after death, there would be no gain because the property would have received a stepped up basis.

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The Decedent’s Final Income Tax Return

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A decedent’s final income tax return must be filed by the Executor by April 15 of the year following death. A joint return may be filed if the decedent’s spouse did not remarry during the year. If no Executor has been appointed by the due date of the return, a joint return must be filed by the surviving spouse. In that case, the later appointed Executor may revoke the surviving spouse’s election to file a joint return and file a separate return for the decedent’s estate within one year from the due date of the return, including extensions.

Liability issues may arise if a joint return is filed, since the executor and spouse become jointly and severally liable for any tax and penalties, unless otherwise agreed. Therefore, the executor should exercise caution before filing a joint return, even if fewer taxes would arise by doing so.

Income tax liability of the decedent which arose before his death constitutes a bona fide debt of the estate. Accordingly, such income tax liability may be deducted on the estate tax return. However, if a joint return is filed, only that portion of the income tax attributable to income for which the decedent was liable may be deducted.  Other expenses incurred by the decedent and paid before death, as well as certain other items, are deductible only on the decedent’s final income tax return. Such expenses and items include (i) medical and other deductible expenses paid prior to death; (ii) capital loss carryovers; (iii) charitable contribution carryovers; and (iv) net operating loss carryovers.

Medical expenses incurred before death but paid after death may be deducted either on the decedent’s final income tax return (provided they are paid within one year of death) or on the estate tax return. To claim the deduction on the final income tax return, the executor must file a statement certifying that the expense was not claimed as a deduction on the estate tax return.

IRC §706(c)(2)(A) provides that the taxable year of a partnership closes with respect to a partner whose entire partnership interest terminates by reason of death. Therefore, the final return includes flow through items for the short year. Under the section 706 regulations, the allocation for the short year is made by effectuating an interim closing of the partnership’s books at the decedent’s death or, if all partners agree, on a pro rata basis based upon the number of days. A similar rule applies with respect to S corporation income.  IRC §1377(a)(2). Allocating on a pro rata basis may be advantageous if it allows the use of carryovers that terminate with the decedent’s death.

The executor may be held personally liable for taxes if a distribution results in an unpaid income or gift tax liability. Liability may exist for the period in which an assessment may be made, i.e., 3 years from the date payment is required, or six years if there is a “substantial omission” (i.e., 25%) of income. Liability may be imposed even if the executor had no actual knowledge of the tax liability. It is sufficient that the executor had knowledge of the facts which would cause a reasonably prudent person to be aware of the tax liability.

Under IRC §6501(d), the executor may request prompt assessment of income and gift taxes attributable to prior returns filed by the decedent. This will shorten the statute of limitations for collection and may benefit the beneficiaries as well as the executor. The executor may also file a written application requesting release from personal liability for the decedent’s income and gift taxes. If the IRS fails to notify the executor of any amount due within 9 months thereof, the executor will be released from liability.

The executor may also incur personal liability for estate taxes. The executor may request a release from liability with respect to any estate tax found to be due within 9 months of making the application if the application is made before the return is filed, or within 9 months of the due date of the return. IRC §2204(a). The executor may remain liable for tax liabilities if beneficiaries seek early distributions. In that case, the executor may seek to protect himself by funding an escrow agreement or reaching some other satisfactory arrangement with the beneficiaries.

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Revision of New York Power of Attorney Law Takes Effect

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Effective 9/1/09, NY General Obligations Law §5-1501, which governs the content and execution of powers of attorney, was revised and amended. Powers executed prior this date remain valid, but are subject to the amended statute.

A power of attorney grants an agent appointed by the principal the authority to make legally binding decisions on the principal’s behalf. This instrument is invaluable should the principal later become incapacitated, since the appointment of a legal guardian, who can also make those decisions, requires plenary court proceedings.

The POA must now be signed, dated and acknowledged not only by the principal, but also by the agent. Under the new law, a POA is durable (i.e., not affected by later incapacity) unless it specifically provides otherwise. If a guardian is later appointed, the agent will account to the guardian rather than to the principal. The new POA contains an optional provision whereby the principal can appoint a “monitor” who may request records of transactions by the agent. The statute also provides for a special proceeding to compel an agent to produce records of receipts. Provisions relating to health care billing should allow the agent access to health care records in accordance with HIPPA privacy requirements.

A new “Statutory Major Gifts Rider” (SMGR), if executed simultaneously with the power of attorney, authorizes the agent to make legally binding major gifts on behalf of the principal. The SMGR must be executed simultaneously with the power of attorney, and with the same formalities governing the execution of a Will. The SMGR may also authorize the agent to “create, amend, revoke, or terminate an inter vivos trust.” The authority of the agent to create joint accounts or to modify a “Totten trust” may also be included in the SMGR. Small gifts ($500 or less) in a calendar year may be made by the agent without a SMGR. The SMGR may be modified to supplement or eliminate the default provisions provided by new law, provided they are not inconsistent with the default SMGR provisions. A conveyance of real property to a bona fide purchaser for less than adequate consideration would require a SMGR, since the conveyance would be in part a gift.

Under GOL §5-1504, acceptance of the statutory “short form” POA by banks and other third parties is now mandatory. A third party may not refuse to honor the power or SMGR without reasonable cause. The statute provides that it is unreasonable for a third party or bank to require its own form, or to object to the form because of the lapse of time between execution and acknowledgment. (Banks had sometimes insisted that their own powers be used, which created a problem where the principal had become incapacitated.) An attorney may certify that a photocopy of a duly executed power is a true copy, and banks must now accept that copy.

The statute requires that the agent, a fiduciary, observe a “prudent person standard of care,” and imposes liability for breaches of fiduciary duty. Fiduciary duties are imposed on agents appointed under all powers of attorney, including those executed prior to the effective date of the new law. The agent must maintain records and must make those records available within 15 days to a monitor, co-agent, certain governmental entities, a court evaluator, a guardian, or a representative of the principal’s estate. The statute expressly provides that the agent is entitled to compensation for his work. A mechanism is provided by which the agent may resign.

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ASSET PROTECTION: ETHICAL CONSIDERATIONS

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New York County Surrogates Court, in In re Joseph Heller Inter Vivos Trust, 613 N.Y.S.2d 809 (1994), approving a trustee’s application to sever an inter vivos trust to “insulate[] the trust’s substantial cash and securities from potential creditor’s claims that could arise from the trust’s real property, observed that “New York law recognizes the right of individuals to arrange their affairs so as to limited their liability to creditors, including the holding of assets in corporate form . . . making irrevocable transfers of their assets, outright or in trust, as long as such transfers are not in fraud of existing creditors.”

Operating a business in corporate form, entering into a prenuptial agreement, executing a disclaimer, or even giving effect to a trust spendthrift provision, are common examples of asset protection which present few ethical issues, primarily because such transfers do not defeat rights of known creditors. However, transferring assets into a corporation solely to avoid a personal money judgment, or utilizing an offshore trust solely to avoid alimony or child support payments, would defeat the rights of legitimate creditors, and would thereby constitute fraudulent transfers.

The ABA’s Model Code of Professional Conduct, DR 7-102, “Representing a Client Within the Bounds of the Law,” provides that “[a] lawyer shall not . . . [c]ounsel or assist his client in conduct that the lawyer knows to be illegal or fraudulent.” Although the Model Code does not define “fraud,” New York, a Model Code jurisdiction, has provided that the term “does not include conduct, although characterized as fraudulent by statute or administrative rule, which lacks an element of scienter, deceit, intent to mislead, or knowing failure to correct misrepresentations which can be reasonably expected to induce detrimental reliance by another.” Therefore, in New York, the prohibition against counseling a client in perpetrating a “fraud” would apparently not prohibit an attorney from assisting a client in transferring property because of the possibility that the transfer might, in hindsight, be determined to have constituted a “fraudulent conveyance”.

Model Rule 8.4 of the ABA’s Model Rule of Professional Conduct provides that it is professional misconduct for a lawyer to “engage in conduct involving dishonesty, fraud, deceit or misrepresentation.” Model Rule 4.4 provides that “a lawyer shall not use means that have no substantial purpose other than to embarrass, delay, or burden a third person.” Conduct involving dishonesty or an attempt to deceive appears to be a readily determinable question of fact. However, conduct employing means having no substantial purpose other than to delay or burden third parties may be a more difficult factual determination.

Connecticut Informal Opinion 91-23 states that “[f]raudulent transfers delay and burden those creditors who would be inclined to try and satisfy their unpaid debts from property of the debtor. It forces them to choose either not to challenge the transfer and suffer the loss of an uncollected debt or to file an action to set aside the transfer. . . If there is no other substantial purpose, Rule 4.4 applies. Where there is another substantial purpose, Rule 4.4 does not apply. For example, where there is a demonstrable and lawful estate planning purpose to the transfer Rule 4.4 would not, in out view apply.”

To minimize risk, the attorney should be careful in performing due diligence prior to engaging in asset protection. Specifically, the attorney should determine (i) the source of the client’s wealth; (ii) the client’s reason for seeking advice concerning asset protection; and (iii) whether the client has any current creditor issues or is merely insuring against as yet unknown future creditor risks. The attorney should also obtain a sworn statement affirming that the client (i) has no pending or threatened claims; (ii) is not under investigation by the government; (iii) will remain solvent following any intended transfers; and (iv) has not derived from unlawful activities any of the assets to be transferred. Since most prohibitions on attorneys involve the attorney having acted “knowingly,” due diligence is the best insurance against future ethical or legal problems.

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Revised New York Criminal Tax Statutes

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Tax professionals preparing 2009 New York State corporate, income, employment and sales tax returns should be alert to statutory changes which create new tax offenses and which impose stricter criminal penalties for existing offenses.  In some cases, tax professionals may be prosecuted under an accomplice theory for aiding or abetting dishonest taxpayers. This memorandum summarizes the new legislation, whose objective is to improve tax compliance and prevent tax evasion by drastically increasing penalties for serious acts of tax evasion and tax fraud.  For more information about the new statute, and for legal guidance, please contact this office.

I.    Introduction

New criminal tax legislation enacted into law on April 7, 2009 marks a sea change in the manner in which New York addresses tax evasion and tax fraud.  Under the new law, serious acts of tax evasion will attract far more severe felony charges.  The new law also gives the Department of Taxation new resources with which to identify and prosecute those engaging in tax evasion.  The new law revises Sections 1800-1848 of the Tax Law, which will continue to apply to criminal acts committed before April 7, 2009.  Under former law, the failure to file a tax return constituted a felony if the taxpayer willfully and with an intent to evade tax failed to file for three consecutive years.  A taxpayer who failed to file for a single year could be charged only with a misdemeanor for not filing regardless of the amount of tax involved.  Conversely, a taxpayer who filed a false return by failing to report income could face prosecution for a class E felony, even if the amount of unreported income involved were small.  Similarly, under former law, taxpayers obtaining refunds by filing fraudulent returns were treated more harshly under the tax law than taxpayers who filed false returns and underpaid their taxes.  Tax Law § 1801(a) creates a new crime, that of “tax fraud,” which applies to all forms of tax evasion, whether accomplished by non-filing, false filing or other fraudulent scheme.  The new law creates eight categories of tax fraud, starting with a class A misdemeanor, rising to a class B felony.

Under former (as well as revised) law, taxpayers were generally required to have acted “willfully” in order to have committed a crime.  However, most tax statutes did not define the term.  Under the new tax law, the term “willfully” is defined; and it creates a uniform minimum mental state required to commit a tax crime.  Tax Law § 1801(c), adopting the federal standard, defines the term “willfully”as “acting with an intent to defraud, intent to evade the payment of taxes or intent to avoid a requirement of [the tax law], a lawful requirement of the commissioner or a known legal duty.”

II.    Eight Categories of Tax Fraud

A.    Tax Law § 1801(a)(1)
Willful Failure to File a Return or Other Required Document

As noted above, under former law the failure to file income or corporate tax returns constituted a felony only if the taxpayer failed to file for three consecutive years.  Under the new law, felony liability arises if the taxpayer (i) fails to file (even for a single year); (ii) intends to evade tax; and (iii) underpays in an amount that meets the monetary threshold.  Accordingly, any willful non-filer who intends to evade tax and evades more than $3,000 in tax liability may now face felony prosecution.

B.    Tax Law § 1801(a)(2),(3)
Willfully and Knowingly Making or Filing a False Return or Report or Supplying False Information

New Tax Law § 1801(a)(2), which addresses the filing of false documents, provides that tax fraud occurs when a person willfully, while
knowing that a return, report, statement or other document under this chapter contains any materially false or fraudulent information, or omits any material information, files or submits that return, report, statement or document with the state or any political subdivision of the state. . .

New Tax Law § 1801(a)(3) addresses the submission of false information to the Department of Taxation and Finance.  Thus, it is tax fraud if a person willfully and knowingly supplies or submits materially false or fraudulent information in connection with any return, audit, investigation, or proceeding or fails to supply information within the time required by or under the provisions of [the tax law or regulations].

The scope of the new law is vast: Nearly every conceivable materially false tax filing or submission would fall within § 1801(a)(2) and (3).  Section 1801(a)(3), which addresses submissions to the Department, include oral submissions made in connection with an audit or investigation.  Thus, the intentional submission of false documentation by the taxpayer or by his representative in order to justify a position would constitute a false submission.  So too would the false assertion by the taxpayer (or his representative) made to an auditor or investigator concerning the existence or non-existence of records.  New Tax Law § 1832(b) makes clear that tax professionals who knowingly provide false documents or who make false assertions on behalf of taxpayers during audit face accomplice liability and will be subject to the same penalties as the taxpayer.

Under former law, knowingly filing a false income or corporate tax return with intent to evade tax constituted a class E felony if the filing resulted in a “substantial understatement” of tax.  Under the new law, the threshold for a substantial understatement was increased from $1,500 to $3,000.  Under the new law, felony liability will arise in all cases where a materially false submission has been made with an intent to evade a tax or to defraud where the false submission results in a tax evasion of more than $3,000.
Note that the new provisions of the Tax Law complement, but do not supersede, existing Penal Law provisions.  Under the Penal Law, knowingly filing a false document with any public office or public servant constitutes a misdemeanor, which rises to felony status if the false filing is made with an intent to defraud the state or any political subdivision.  No minimum monetary threshold applies to the Penal Law statute.  Thus, a taxpayer who files a false income tax return which defrauds New York of less than $3,000 would be exposed to misdemeanor liability under the new tax law, but felony liability under the Penal Law.

C.    Tax Law § 1801(a)(4)
Willfully Engaging in a Scheme to Defraud the State in Connection With Any Matter Under the Tax Law

Tax Law  § 1801(a)(4) supplements §§ 1801(a)(2) and (a)(3) by ascribing tax fraud status to acts which do not involve filing a false document or making a false submission to the Department.  Thus,  § 1801(a)(4) provides that a person (not necessarily a taxpayer) commits tax fraud when he willfully
engages in any scheme to defraud the state or a political subdivision . . . by false or fraudulent pretenses, representations or promises as to any material matter, in connection with any tax imposed. . .

Although similar to language in Penal Law statutes, the Tax Law is more strict than its Penal Law analogue in that it does not require a “systemic ongoing course of conduct,” as does the Penal Law.  However, the Tax Law is less strict than the Penal Law in that false representations must be with respect to a “material” matter.  The new tax statute is intended to reach persons engaging in schemes such as cigarette tax evasion which involve persons who are not required to file returns or remit taxes.  Tax Law § 1801(a)(4) is intended to act synergistically with new classes of tax felonies, described below.

D.    Tax Law § 1801(a)(5)
Willfully Failing to Remit Taxes Collected on Behalf of the State

Withholding taxes collected from employees and sales taxes collected from customers constitute trust fund taxes.  While fiduciaries who misappropriate these funds have always subject to prosecution under the Penal Law for larceny, prosecution under the Tax Law has been  problematic, as liability for employers who failed to remit employment taxes was limited to a misdemeanor under the Tax Law, regardless of the amount of payroll taxes collected and not remitted; and the failure of a tax vendor to remit collected sales tax was not a criminal act under the Tax Law.  Under new Tax Law § 1801(a)(5), tax fraud occurs when a person willfully “fails to remit any tax collected in the name of the state or on behalf of the state . . . when such collection is required under this chapter.”  Therefore, resort to the Penal Law is no longer necessary to seek felony prosecution for crimes involving failure to remit sales or withholding taxes.

E.    Tax Law § 1801(a)(6)
Willfully Failing to Collect a Sales, Excise or Withholding Tax That is Required to Be Collected

Under former Tax Law § 1817(c), the failure of employers to collect employment tax, and the failure of vendors to collect sales tax, constituted a misdemeanor.  Tax Law § 1817(c)(2) provided that the failure to collect $10,000 in sales tax or the failure to collect $100 in sales tax on ten or more occasions constituted a class E felony.  Under revised Tax Law § 1801(a)(6), the willful failure to collect tax when required constitutes tax fraud.  If taxes not collected exceed $3,000 in one year, felony liability attaches; otherwise, the tax fraud constitutes a misdemeanor.

F.    Tax Law § 1801(a)(7)
Willfully and With an Intent to Evade Any Tax, Failing to Pay a Tax Due

Under new Tax Law § 1801(a)(7), the taxpayer who willfully and with intent to evade tax fails to pay such tax commits tax fraud.  The new law imposes a stricter standard for prosecution than the former law in that the failure to pay must be both willful and with an intent to evade tax.  Thus, those taxpayers who file but cannot pay the tax will not be subject to criminal liability.  However, for those taxpayers whose failure to file does meet the more exacting standard, felony liability may attach if the amount of the underpayment meets the monetary limits in the felony tax fraud sections (described below).  This tax law provision will provide prosecutors with an avenue of recourse to address those taxpayers who file accurate sales or income tax returns but who unjustifiably fail to satisfy those reported tax liabilities, though not without the means to do so.

G.    Tax Law § 1801(a)(8)
Issuing False Exemption Certificates

New Tax Law § 1801(a)(8) provides that a tax fraud act includes one where a party willfully

issues an exemption certificate, interdistributor sales certificate, resale certificate, or any other document capable of evidencing a claim that taxes do not apply to a transaction, which he or she does not believe to be true and correct as to any material matter, which omits any material information, or which is false, fraudulent, or counterfeit.

The primary difference in the new law is that (i) a willful omission in exemption certificate constitutes a violation of law and (ii) felony liability can attach (previously only misdemeanor liability arose) if the taxpayer possesses the intent to evade tax and as a result of the fraudulent act underpays an amount which meets the monetary thresholds specified in the felony tax fraud sections.

III.    Felony Tax Fraud Classifications

For an act of tax fraud to constitute a felony under the new tax law, three separate requirements must be met: First, the taxpayer must act willfully; that is, the taxpayer must intend to commit the prohibited act.  Second, the taxpayer must possess an intent to defraud New York State.  The new law attempts to distinguish between those who choose not to pay tax liabilities and those who are without the means to pay their tax liabilities.  It would appear that those who are simply unable to pay their tax liability cannot be guilty of tax fraud.  Therefore, a taxpayer who reports income and files a return, but fails to pay tax by reason of an inability to do so, has not committed tax fraud.  The third requirement for felony tax liability consists of meeting the monetary thresholds.  The chart below indicates the monetary threshold for various classes of tax felonies, and compares them to other felonies.  Note that for the lower two classes of tax felonies, the monetary threshold is higher for tax fraud than for crimes arising under the Penal Law.  Perhaps most significant in the new felony tax fraud classification system is the fact that those persons proven to have engaged income or corporate tax evasion in amounts exceeding $10,000 will for the first time be exposed to serious felony liability.  Those committing sales or withholding tax evasion charges have long been subject to serious felony prosecution for larceny under the Penal Law.  Similarly, those taxpayers filing a false return, but who fail to reach the monetary threshold for felony tax fraud may continue to be prosecuted under the Penal Law for “Offering a False Instrument for Filing,” which is a class E felony.

Felony Classification    Degree    Tax Fraud/Health Care Fraud    Larceny/Welfare/Insurance
E     4th     > $3,000    > $1,000
D     3rd     > $10,000    > $3,000
C    2nd     > $50,000    > $50,000
B    1st     > $1,000,000    > $1,000,000

IV.    Aggregation

In determining the class of felony, tax liabilities evaded within a single-year period may be aggregated, but not those occurring over more than one year.  However, this rule applies only with respect to aggregation under the Tax Law.  Aggregation of sales tax or withholding tax liabilities over multiple years may occur where larceny prosecution is commenced under the Penal Law.

V.    Monetary Penalties

New Tax Law § 1800(c) increases monetary penalties for tax felonies to the greater of (i) double the amount of the underpaid tax liability or (ii) $50,000 for individuals or $250,000 for corporations.  Fines for misdemeanors relating to tax fraud remain unchanged at $10,000 for individuals and $20,000 for corporations.

VI.    Venue

Under new subsection (m) of N.Y. Criminal Procedure Law § 20.40(4), the taxpayer may be prosecuted in the county where the economic activity to prosecute the tax crime arose.  This statutory change results from the recognition that taxpayers may be involved in economic activity in one county that results in the filing of a tax return in a different county.

VII.    Subpoenas

New Tax Law § 1831 makes the willful failure to comply with a subpoena issued by the Department of Taxation a misdemeanor.  Previously, misdemeanor liability attached to the willful failure to comply with some, but not all, administrative subpoenas issued by the Department.  This is significant in that the number of subpoenas issued in criminal fraud investigations rose from 349 in fiscal year 2007-2008 to 1,320 in fiscal year 2008-2009.

VIII.    Tax Preparers

New Tax Law § 32 requires tax preparers who are not licensed attorneys or certified public accounts to register with the Department as tax preparers and to sign every return which they prepare.  Under new Tax Law § 1833, the failure to register or to sign a return is a misdemeanor.

IX    Conclusion

In fiscal year 2008-2009 the Department opened 2,078 criminal fraud investigations, up from 928 cases in 2007-2008.  Criminal fraud prosecution referrals saw a commensurate increase.  The new Tax Law provisions provide prosecutors and the Department with a vast arsenal of new weapons with which to counter tax fraud at all levels.  In light of New York’s current fiscal situation, tax professionals should be prepared to defend taxpayers not liable for tax fraud against possible acts of overreaching under the new law by the Department, the Attorney General, or by local prosecutors.

Very truly yours,
/s/
David L. Silverman

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Business Succession Planning Involving Family Members

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Business succession planning involving family members presents  unique challenges, since liquidity needed to pay estate tax or to fund a legacy for nonparticipating family members may exceed that which the business generates. A buy-sell agreement can establishing the price at which participating family members may purchase the business, or a mechanism in which the interest of nonparticipating family members may be redeemed by the entity. If negotiated at arms-length, the price determined under a buy-sell agreement may control for estate tax purposes.

Permissible transferees under a buy-sell agreement may also include other owners of the entity. If a “cross-purchase” agreement is used, the continuing owners will acquire the withdrawing owner’s interest at a price determined under the agreement. A significant advantage to a cross-purchase agreement is that under IRC § 1012, the basis of the surviving owner’s interest is increased by the price paid. Under a “redemption agreement,” the entity itself redeems the owner’s interest at a price determined under the agreement. A management agreement, which defines the rights, powers and responsibilities of each equity owner, often supplements a buy-sell agreement.

Business equity may pass equally to all children, or only to children active in the business, with equalizing transfers of non-business assets to nonactive children. Determining the amount of the equalizing transfer may be difficult, as nonactive children may feel that dividing assets based upon values as finally determined for estate tax purposes may be unfair. Even if fair equalizing values can be determined, nonbusiness assets may be insufficient to provide equal shares to nonactive children. In this case, all or part of the business could be sold to active children, or business equity could pass equally to all children with built-in redemption provisions enabling nonactive children to “put” their business interest to the company at a future time. The put right could be triggered upon a change in ownership or a change in control.

At times, the owner may wish to cede management of the business during his lifetime to family members without disposing of his equity in the company. Future economic benefits could be retained by establishing a mandatory dividend or distribution policy with respect to a retained membership interest or stock ownership. Corporations other than S corporations could have two classes of stock with the class retained by the retiring owner possessing preferential dividend and distribution rights. An S corporation could engage in a tax-free recapitalization creating voting and non-voting interests without violating the single-class-of-stock rule. By selling non-voting interests, the retiring owner could continue to exercise control over dividends and distributions. IRC § 2036 would not apply to a bona fide sale for adequate and full consideration.

An owner with business expertise could enter into a consulting or non-compete agreement with the business which would provide continuing income to the retiring partner. Payments under a consulting agreement are deductible by the business. Unless the retiring owner is an independent contractor, compensation received would be subject to self-employment tax. If employment tax liability arises, the IRS is likely to be indifferent to the level of compensation. Therefore, an owner willing to provide continued services can be divested of ownership interest in the company for legal and estate tax purposes, while continuing to receive a steady stream of income. Payments under a non-compete agreement are amortizable by the business over 15 years under IRC § 197 and although includible as ordinary income, are not subject to employment tax.

An executive bonus plan could be used to fund a nonqualified private pension, such as a life insurance policy. Since such a plan is not tax-advantaged, it could discriminate in favor of any employee. For income tax purposes, the premium payments would be treated as bonuses (or guaranteed payments in the case of a partnership or LLC). Such payments would be deductible by the business and includible as compensation by the owner.

Various trust arrangements may facilitate a plan of business succession. By selling an ownership in the business to a grantor trust, the retiring owner can remove the value of the business, as well as its appreciation, from his estate with no adverse gift or income tax consequences. The promissory note issued by the trust as consideration for the business interest purchased could provide for a low rate of interest at the applicable federal rate. If a self-canceling feature were employed, nothing would be included in the seller’s estate at his death; however, the rate of interest used would have to be higher to compensate for the self-canceling feature.

To appease family members who continue to participate in the business and want no interference from nonparticipating family members, the equity of nonparticipating members could be transferred to a voting trust, which would issue new trust certificates representing the transferred interest. Voting rights would become vested in the trustee. Other inter vivos trust arrangements may be used to hold and pass equity among family members. For example, a revocable trust agreement may specify how the business equity will be distributed should the owner becomes incapacitated.

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Tax Court Holds Single Member LLC Not Ignored for Gift Tax Purposes

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In Pierre v. Com’r, 133 T.C. No. 2 (8/4/09), a sharply divided Tax Court with five dissenting judges held that a single member LLC, though ignored for income tax purposes, must be respected as a separate entity for gift tax purposes.

[Susan J. Pierre formed Pierre Family, LLC, a single-member LLC, on July 13, 2000. On September 15, 2000, she transferred $4.25 million in cash and securities to the LLC. On September 27, she gave 19 percent of her LLC membership interest to two trusts and sold 81 percent of her interest to those two trusts in exchange for a promissory note. Discounts of 30% were taken for lack of control and lack of marketability. A gift tax return was filed.]

On examination, the IRS disallowed the discount and asserted a deficiency, arguing that the LLC should be ignored for gift tax purposes, and that the membership interests gifted and sold should instead be treated as transfers of cash and marketable securities for which no discounts were available. The promissory notes evidencing the sale of LLC interests were therefore insufficient in amount, causing the “sale” to be part unreported taxable gift. The gift of the membership interests, although reported, was also undervalued. These undervaluations resulted in a deficiency.]

The first issue was nature of the property interest transferred. The taxpayer argued that state law rather than federal law determines the nature of a taxpayer’s transferred ownership. Under NY LLC Law 601, a membership interest in an LLC is personal property, and a member has no interest in specific property of the LLC. The Tax Court agreed, observing that “a fundamental premise of transfer taxation is that State law creates property rights and interests, and Federal tax law then defines the tax treatment of those property rights.” Under New York law, the taxpayer did not possess a property interest in the underlying assets of Pierre, LLC. Consequently, gift tax liability was properly determined by the value of the transferred interests in the LLC, rather than by the value of the underlying assets.

The Tax Court then summarily disposed of the IRS argument that the LLC should be ignored for gift, as well as income, tax purposes:
“If the check-the-box regulations are interpreted and applied as respondent contends, they go far beyond classifying the LLC for tax purposes. The regulation would require that Federal law, and not State law, apply to determine property rights and interests transferred by a donor for valuation purposes under the Federal gift tax regime. . .To conclude that because an entity elected the classification rules. . .the long-established Federal gift tax valuation regime is overturned as to single-member LLCs would be ‘manifestly incompatible’ with the Federal estate and gift tax statutes as interpreted by the Supreme Court.”

The dissent argued that (i) “the plain language of the regulations requires Pierre LLC to be ‘disregarded as an entity separate from its owner’”; (ii) federal law, in the form of check-the-box regulations, determines the nature of the property rights and interests transferred; and that (iii) that such an interpretation was not “manifestly incompatible with the gift tax statutes.”

Although Pierre reinforced the proposition that single-member LLCs are indeed entitled to valuation discounts, those entities, while useful for income tax purposes, are sometimes less than perfect for other legal purposes, since there is a temptation — as clearly evidenced by the dissenting opinion in this case — to ignore the LLC for other legal and tax purposes as well. The problem encountered in Pierre would not have arisen had a multi-member LLC been utilized. Of particular interest is that in other respects, the taxpayer was astute: an independent valuation appraiser was retained to compute the appropriate discounts, and LLC formalities were observed.

¶ The 5th Circuit recently held that the transfer of assets owned by Linda Evans and the Estate Robert C. Evans, Jr., to a limited partnership following a Tax Court judgment constituted a fraudulent transfer under the Texas Fraudulent Transfer Act. Since the United States was not bound by state statutes of limitations in fraudulent conveyance actions, the statute’s four-year limitations period was inapplicable. U.S. v. Evans, No. 08-51054, (August 18, 2009).

¶ In Estate of McCoy, TC Memo, 2009-61, the decedent’s will and trust provided that specific bequests were to be paid from the residuary estate. Different definitions of “residuary” in the governing instruments created ambiguity over the tax clause. The estate apportioned all estate taxes to the specific bequests, rather than to the marital bequest. Although the IRS argued that the marital share was the proper source of payment, the Tax Court ruled that unless the will clearly provides otherwise, the state apportionment statute controls. Since Utah’s apportionment statute equitably apportions taxes to property that generates the tax, no estate tax was imposed on the marital bequest.

¶ In Bennett v. Com’r, TC Memo 2008-251, the IRS rejected the taxpayer’s offer in compromise even though the amount offered was ten times that which the IRS determined it could currently collect. The taxpayer, who had failed to file for five years, and had rejected an IRS counteroffer, argued that the IRS abused its discretion, since IRS guidance provides that an offer should be accepted when “it reasonably reflects collection potential.” Noting that the regulations do not compel the IRS to accept any particular offer, the Tax Court concluded that “guidelines are in the end just that.”

¶ It is well settled that a settlor’s interest in a domestic asset protection trust (“APT”) is excluded from the bankruptcy estate under §§541(c)(2) and 548(e) of the Bankruptcy Code. Will distributions of income or principal from the trust become part of the bankruptcy estate? The answer appears to be no. To be included in the bankruptcy estate, a domestic APT distribution must satisfy two requirements under §541(a)(5)(A): First, the debtor’s receipt or entitlement to receipt must occur within 180 days after the filing of the bankruptcy petition. Second, the receipt must arise from a “bequest, devise, or inheritance.” Since an APT is an inter vivos trust, it is doubtful that any distribution would satisfy these requirements. Therefore, a trustee in bankruptcy could not likely reach assets distributed from an APT.

¶ Since the IRS imposes greater scrutiny on transfers and discounts involving family entities, the lack of substantial nontax reasons for forming these entities may predispose these transfers to later examination. Estate of Jorgensen, T.C. Memo, 2009-66, illustrates the danger of ignoring case law, formalities, and proper maintenance when utilizing family entities for estate planning. Discounts of 35% were taken on gifts without obtaining an independent discount appraisal. The partnership bank account was used to make cash gifts to family members and to pay personal expenses. Partnership formalities were not followed, since a requirement that distributions be pro rata was ignored. The son borrowed money for personal expenses. Non-tax reasons for forming the limited partnerships were lacking. The Tax Court concluded that the use of a significant portion of partnership assets to discharge the taxpayer’s obligations evidenced a retained interest in the assets of the partnership.

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2009 REGS., RULINGS AND PRONOUNCEMENTS OF NOTE

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I.  Treasury Regulations & Proposals

¶  Treasury issued final regulations limiting the estate tax deduction for unpaid claims and expenses. With respect to decedents dying on or after October 20, 2009, an estate may deduct an expenditure only if the claim or debt is actually paid. Under the new regs, the amount of claim or expense may be determined by (i) court decree; (ii) consent decree; or (iii) settlement. No deduction is allowed to the extent a claim or expense is or could be reimbursed by insurance. Notice 2009-84.

Nevertheless, several exceptions exist to the rule requiring actual payment. If a potential for reimbursement exists, the claim may still be deductible if the executor provides a “reasonable explanation” of why the burden of collection would outweigh the anticipated benefits of collection. Another exception provides that a claim or expense may be deducted by the estate if the amount to be paid is ascertainable with “reasonable certainty.” No deduction may be claimed for claims that are contested or contingent.

¶ Although the IRS has been  successful in challenging gift and estate valuation discounts with arguments premised on §2036, §2704(b) has rarely aided the IRS in litigation in the twenty years since its enactment. Treasury’s 2010 budget proposal includes a provision that would expand the scope of §2704(b). Section 2704(b) ignores in valuing an interest in a closely held entity any “applicable restriction” on liquidation that would lapse or could be removed after the transfer. Restrictions in governing agreements, if not ignored, increase estate and gift tax discounts. Under the proposal, a new category of “disregarded restrictions” would be ignored under §2704(b). Disregarded restrictions would include limitations on the owner’s right to liquidate the interest if the limitations are more restrictive than a standard identified in the regulations, even if they are no more restrictive than those imposed by state law. (Most states have enacted “friendly” statutes to take advantage of the “no more restrictive than state law” language in §2704(b), which has made it possible for estate planners to avoid the application of the statute.)

¶   Treasury’s 2010 budget proposal includes a requirement that all GRATs have a term of not less than 10 years. This limitation would be intended to ensure that the transaction has at least some downside risk. The 10 year requirement would make it unlikely that many taxpayers over 75 years old would utilize a GRAT. Instead, those individuals would likely use sales to grantor trusts to shift appreciation in transferred assets to donees. Note that the proposal would not affect the use of “zeroed-out” GRATS, where the initial taxable gift is negligable.

¶  Treasury has also proposed that taxpayers who receive property by gift or by bequest from a decedent must use the gift or estate tax value for future income tax purposes, even if they disagree with that value. Thus, a taxpayer who receives property from a decedent would be required to use as his basis that reported for estate tax purposes. Similarly, a taxpayer receiving property by gift would be required to use the donor’s basis as reported for gift tax purposes.

¶   Treasury announced new actuarial tables to reflect increased longevity. The new tables increase the value of lifetime interests and decrease the value of remainders or reversionary interests. T.D. 9448.

II.        Private Letter Rulings

¶   In PLR 200944002, the grantor created a self-settled spendthrift trust for the benefit of himself, his spouse and his descendants. The trust provided that the trustees could not be related or subordinate to the grantor or his spouse, and that the grantor had no right to remove the trustees. Under state law, a trust instrument containing such restrictions prevents a creditor existing when the trust is created, or subsequent creditor, from satisfying a claim out of the beneficiary’s interest in the trust, unless (1) the trust is revocable by the grantor without the consent of an adverse party; (2) the grantor intends to defraud a creditor; (3) the grantor is in default of a child support obligation; or (4) the trust requires that all or part of the trust’s income or principal, or both, must be distributed to the grantor.

The IRS concluded that the transfers to the trust were completed gifts for gift tax purposes since the grantor had no power to revest beneficial title. Furthermore, the trust assets would not be includible in the grantor’s gross estate since the grantor’s retained power to substitute assets did not constitute a reserved power to alter beneficial enjoyment by reason of the trustee’s fiduciary obligations.

¶   In PLR 200919003, the decedent’s revocable trust created a marital trust intended to be a QTIP trust. However, the language creating the power made it both lifetime and testamentary. Noting that state law permitted reformation of a trust to correct a “scrivener’s error” which had occurred, the IRS stated that the reformation would be accepted for estate tax marital deduction purposes.

III.     Chief Counsel Advisories & Notices

¶   In CCA 200923024, the Office of Chief Counsel analyzed a case where taxpayer transferred S corporation stock to a partnership, and then formed an irrevocable nongrantor trust. An IRC § 754 election was made, stepping up the inside basis of S corporation assets. After this election, nongrantor trust status was terminated, and the trusts were converted into grantor trusts under IRC § 674. The CCA concluded that although the transactions were “abusive,” they were not taxable since the conversion of a nongrantor trust to a grantor trust is not deemed to be a transfer for income tax purposes. The CCA has positive implications for asset sales to grantor trusts, where a “switch” in the trust instrument can be inserted to turn grantor trust status on and off.

¶  In Interim Guidance Memorandum 04-0509-009 (May 8, 2009), the IRS directed its estate tax attorneys to consider imposing preparer penalties under IRC §6694. The guidance states that during every examination, estate tax attorneys should determine if preparer penalties are appropriate, based on oral testimony and/or written evidence adduced during the examination process.

¶  CCA 200937028 confirmed that assets sold to an intentionally defective grantor trust receive no basis step up at the Grantor’s death. The IRS quoted Regs. §1014-1(a), and concluded that “it would seem that the general rule is that property transferred prior to death, even to a grantor trust, would not be subject to section 1014, unless the property is included in the gross estate for federal estate tax purposes as per section 1014.”

¶   Notice 2008-13 provided guidance concerning the imposition of return preparer penalties. Notice 2009-5 provides that tax return preparers may apply the substantial authority standard in the 2008 Tax Act, or may continue to rely on Notice 2008-13, which provides interim guidance.

IV.      New York Developments

¶    New York imposes estate tax on a pro rata basis to nonresident decedents with property subject to New York estate tax. NYS-DTF Memorandum TSB-M-92 provides that “New York has long maintained a tax policy that encourages nonresidents to keep their money, securities and other intangible property in New York State.” TSB-A-85(1) further provides that shares of stock of a New York corporation held by a nonresident are not subject to New York estate tax since shares of stock are considered intangible personal property.

Still, TSB-A-08(1)M, provides that an interest of a nonresident in an S Corporation which owns a condominium in New York is an intangible asset provided the S Corporation has a legitimate business purpose. Presumably, if the S Corporation had only a single shareholder, and its only purpose was to hold real estate, New York could attempt to “pierce the veil” of the S Corporation and subject the condominium to New York estate tax in the estate of the nonresident.

¶   Assume a valid QTIP election is made on a New York estate tax return, but the surviving spouse is no longer a resident of New York at her death and the trust has no nexus to New York. Will New York seek to “recoup” the estate tax deduction claimed on the first spouse to die in a manner similar to the way in which California’s “clawback” tax recoups deferred tax in a like-kind exchange if out-of-state replacement property is later sold? Apparently not, provided the surviving spouse is a bona fide nonresident of New York at her death.

Would the state in which the surviving spouse dies have a right to tax the assets in the QTIP trust? Also, probably not. Generally, a QTIP trust is not includible under IRC §2036 in the estate of the surviving spouse if no QTIP election is made. Although a QTIP election was made in New York, no QTIP election was made in the state in which the surviving spouse dies. Therefore, that state would seem to have no basis to impose estate tax on the assets in the QTIP trust.

[Note, however, that if the state in which the surviving spouse dies imposes an inheritance tax (such as that imposed by Pennsylvania) then this tax would not be avoided, since an inheritance tax is imposed on the transferee, rather than on the estate.]

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DOMESTIC ASSET PROTECTION TRUSTS

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I.      Introduction

Many estate planning trusts also possess significant asset protection features. A qualified personal residence trust (“QPRT”) results when an interest in real property, which could be attached by a creditor, is converted into a mere right to reside in the residence for a term of years. The sale of an asset to a “defective” grantor trust in exchange for a promissory note converts the asset into an instrument which may be unattractive to a creditor if it provides only for interest payments.

Since these trusts are ubiquitous in estate planning, they are less likely to be vulnerable to a claim that they were formed with an intent to hinder, delay or defraud creditors. Less commonly, trusts are called upon to achieve purely asset protection objectives. Their effectiveness in this role appears to militate in favor of their greater use.

Asset protection features of an asset protection trust (“APT”) may arise by virtue of a discretionary distribution provision in the trust. The trust may provide that the Trustees “in their sole and absolute discretion may pay or apply the whole, any portion, or none of the net income for the benefit of the beneficiaries.” Alternatively, the Trustees’ discretion may be limited by a broadly defined standard, i.e., “so much of the net income as the Trustees deem advisable to provide for the support, maintenance and health of the beneficiary.”

The effect of a discretionary distribution provision on the rights of a creditor are profound. If the trust provides that (i) the beneficiary cannot compel the trustee to make distributions, and assuming that (ii) the rights of a creditor can be no greater than those of the beneficiary, it follows that (iii) a creditor cannot compel the trustee to make distributions. Therefore, properly limiting the beneficiary’s right to income from the trust may well determine the extent to which trusts assets are protected from the claims of creditors.

Failure to properly limit the beneficiary’s right to income from an APT can have deleterious tax consequences if the creditor is the IRS. TAM 0017665 stated that where the taxpayer had a right to so much of the net income of the trust as the trustee determined was necessary for the taxpayer’s health, maintenance, support and education, the taxpayer had an identifiable property interest in the trust which was subject to a federal tax lien. Since the discretion of the trustee was broadly defined, and subject to an “ascertainable standard” rather than being absolute, the asset protection feature of the trust was diminished.

If asset protection is a major objective, it would be inadvisable to draft a trust in which the trustee’s obligation to distribute income is subject to an ascertainable standard, rather than within the trustee’s absolute discretion. However, that is not enough: Even if the trustee’s discretion is absolute, a court may review the trustee’s discretion. Fortunately, courts have generally been disinclined to substitute their judgment for that of the trustee, even where the trustee’s discretion is absolute. The Uniform Trust Code is in accord, providing that a creditor of a beneficiary may not compel a distribution even where the trustee has abused his discretion.

A beneficiary should not be named sole trustee of his own discretionary APT, since the interest of a beneficiary who has discretion to determine his own distributions may be attached by a creditor. On the other hand, if the sole trustee — even a beneficiary — has no discretion with respect to distributions made to himself, his interest in the trust would not likely be subject to attachment by a creditor. However, amounts actually distributed could be reached.

II.      Spendthrift Trusts

Even if the trustee’s discretion is absolute, the APT should also contain a valid spendthrift clause, since it is not enough for asset protection purposes that a creditor be unable to compel a distribution. The creditor must also be unable to attach the beneficiary’s interest in the trust. A spendthrift provision prevents the beneficiary from voluntarily or involuntarily alienating his interest in the trust. The Supreme Court, in Nichols v. Eaton, 91 U.S. 716 (1875), recognized the validity of a spendthrift trust, holding that an individual should be able to transfer property subject to certain limiting conditions.

A spendthrift trust will thus protect a beneficiary from (i) his own profligacy or bankruptcy; (ii) his torts; and (iii) many of his creditors, (including his spouse). No specific language is necessary to create a spendthrift trust, and a spendthrift limitation may even be inferred from the intent of the settlor. Still, it is preferable as well as customary to include spendthrift language in a trust. A spendthrift provision may also provide that required trust distributions become discretionary upon the occurrence of an event or contingency specified in the trust. Thus, a trust providing for regular distributions to beneficiaries might also provide that such distributions would be suspended in the event a creditor threat appears.

A few exceptions could reduce the effectiveness of a spendthrift trust. As indicated above, if a beneficiary is also the sole trustee of a discretionary spendthrift trust, the trust will be ineffective as against creditors’ claims. Other exceptions are in the nature of public policy exceptions. Thus, assets in a spendthrift trust may be reached to enforce a claim against the beneficiary for support of a child. Courts might also invalidate a spendthrift trust to satisfy a judgment arising from an intentional tort. Furthermore, a spendthrift trust would likely be ineffective against claims made by the government relating to taxes, since the strong public policy in favor of the government collecting taxes may be deemed to outweigh the public policy of enforcing spendthrift trusts.

III.     “Self-Settled” Spendthrift Trusts

A “self-settled” trust is one which the beneficiary creates for his own protection. Here, the settler is either one of the beneficiaries or the sole beneficiary of the trust. A self-settled trust may also be spendthrift. Prior to 1997, neither the common law nor the statutory law of any state permitted a self-settled trust to be endowed with spendthrift trust protection.

However, since 1997, five states, including Delaware and Alaska, have enacted legislation which expressly authorizes the use of self-settled spendthrift trusts. A self-settled spendthrift trust, if established in one of these five states, may effectively allow an individual to put assets beyond the reach of creditors while retaining some control over and access to trust assets. These states now compete with jurisdictions such as the Cayman Islands and Bermuda, which for many years have been a haven for those seeking the protection of a self-settled spendthrift trust.

Most states, including New York, continue to abhor self-settled spendthrift trusts. This is true even if another person is named as trustee and even the trust is not created with an intent to defraud existing creditors. New York’s strong public policy against self-settled spendthrift trusts is evidenced in EPTL §7-3.1, which provides that “[a] disposition in trust for the use of the creator is void as against the existing or subsequent creditors of the creator.” Still, there appears to be no reason why a New York resident could not transfer assets to the trustee of a self-settled spendthrift trust situated in Delaware or in another state which now permits such trusts.

Trust arrangements nominally not self-settled spendthrift trusts, but which seek to achieve that status by indirect means, will likely fail in that desired objective. Thus, a “reciprocal” or “crossed” trust arrangement, in which the settlor of one trust is the beneficiary of another, would likely offer little or no asset protection. (In fact, the “reciprocal trust doctrine” has often been invoked by the IRS to defeat attempts by taxpayers to shift assets out of their estates.)

Important estate planning objectives may be furthered by establishing an APT. However, normal estate tax rules must be considered. For example, the estate of a settler who retains the right to receive trust distributions will be required to include trust assets in the estate under IRC § 2036. This problem will not be avoided even if the “right” to receive income is within the discretion of the Trustees, since it is the retained right which causes inclusion. However, by utilizing a domestic APT in which the settler retains no right whatsoever to income, inclusion under IRC § 2036 should be avoided.

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2009 Gift & Estate Tax Decisions of Note

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I.    Valuation Discounts

In Estate of Litchfield, T.C. Memo 2009-21, the Tax Court generally approved the lack of control (14.8%), lack of marketability (36%), and built-in capital gains (17.4%) discounts for minority interests in closely-held S corporation stock owned by the decedent at his death. In reaching its holding, the Tax Court emphasized that while the taxpayer’s appraiser had interviewed corporate officers, the IRS appraiser relied solely on outside data.

In Estate of Hester, 99 AFTR 2d 2007-1288, aff’d per curiam, 102 AFTR 2d 2008-6716, cert. denied sub nom., 128 S.Ct. 2168 (2009), the decedent breached his fiduciary obligations with respect to a trust created at the death of his wife by transferring all of the trust assets into his own name. He then pledged the distributed trust assets as security for margin loans, withdrew over $450,000 in cash, and collected $280,000 from a promissory note held by his late wife’s estate. Despite this misappropriation of funds, no one appeared at a “debt and demands” hearing to oppose the distribution of assets pursuant to his will.

The decedent’s estate paid $2.727 million in estate taxes, and made a claim for refund, which was denied by the IRS. The court ruled that since no claim was made against the estate and none was “reasonably expected,” the estate was not entitled to a deduction under §2053(a)(3) as a claim against the estate, or under §2053(a)(4) as a debt of the decedent.

Note: The Estate chose to pay the tax and then file a claim for refund in the Virginia District Court, rather than proceed to Tax Court, where the deficiency may be litigated before any obligation to pay arises. This strategy, as will be seen below, has been successful in a number of cases.

A divided Tax Court, in Pierre v. Com’r., 133 T.C. No. 2 (2009) held that a single member LLC, though ignored for income tax purposes, must be respected as a separate entity for gift and estate tax valuation discount purposes. The IRS was unsuccessful arguing that the election under the “check-the-box” regulations to treat the entity as being disregarded for tax purposes should also result in its being disregarded for gift and estate tax valuation discount purposes. The case illustrates the danger of using single member LLCs — or any disregarded tax entity such as a single-shareholder S corporation — if the objective is to validate estate or gift tax valuation discounts.

The Ninth Circuit, in Stone v. U.S., 103 AFTR2d 20091379, affirmed a decision of the Tax Court limiting the estate’s discount to a collection of valuable artwork to 5%. The IRS was successful in limiting the lack of marketability discount to the costs of a partition action.

II.     IRC § 2036 Inclusion

IRC Section 2036 continued to play a decisive role in many decisions involving valuation discounts.

¶  In Estate of Hurford, T.C. Memo 2008-278, the Tax Court disallowed all discounts, and included the undiscounted value of the underlying assets in the decedent’s estate. The case had bad facts. Employment agreements with children were never executed, stock certificates, regulations, and organizational minutes of LLCs were unsigned, FLP operation was sloppy, assets of marital trusts were withdrawn to fund FLPs in violation of trust provisions, and the surviving spouse, who had sole check-writing authority over the FLP accounts, transferrred money without regard to the interests of the partners and without recording the transactions.

¶    The IRS was also victorious in Estate of Jorgensen, T.C. Memo 2009-66. Col. and Ms. Jorgensen funded a Virginia limited partnership with marketable securities. Their children were named as general partners even though they made no contributions to the partnership. The Tax Court held that the transfer to the partnerships was not a bona fide sale for adequate and full consideration so as to come within the exception under IRC § 2036(a), since there was no “legitimate and significant nontax reason for creating the family limited partnership.”

¶  In Estate of Miller, T.C. Memo 2009-66, the decedent created an FLP and gifted interests to her children. The FLP hired a corporation managed by her son to manage investments. At her death the estate claimed a 35% discount for FLP interests held in trust. The Tax Court held that securities transferred in 2002 were not includible in the decedent’s gross estate, and approved the discount for lack of marketability. However, later transfers made when the decedent was in declining health were found to be includible in the gross estate since they were not made with a “legitimate and substantial nontax purpose.”

¶  In Estate of Keller, 104 AFTR 2d 2009-6015 (S.D. Tex.), the decedent, who had been ill, signed various documents organizing LLCs before her death. Some organizing documents contained blanks because of uncertainty about fair market values. The decedent died before accounts were opened and the LLCs were formally funded. Believing that the LLCs had not been properly formed, the estate took no discounts and paid estate taxes of $147.8 million.

Thereafter, the decedent’s son learned of the decision in Church v. U.S. 85 AFTR 2d 2000-804 (W.D. Tex. 2000), which had allowed valuation discounts for an unfinished family partnership. The estate filed a claim for refund, which the IRS denied. Holding for the estate and allowing the discounts, the District Court in Texas found that the decedent intended to fund a valid Texas LLC whose purpose to protect family assets. Since any estate tax savings which accrued were merely incidental, the transfers were found to be for full and adequate consideration.

¶  In Estate of Malkin, T.C. Memo 2009-212, the decedent created an FLP and assigned to it stock of a company in which he was the CEO. The FLP interests were then sold to trusts for a self-cancelling installment note. The assets were later pledged to secure a bank debt. The Tax Court held that since the stock was used to secure a personal debt, the decedent retained the right to beneficial enjoyment of the stock, resulting in inclusion in his gross estate under IRC 2036(a).

¶   In Estate of Murphy, 2009 WL 3366099 (W.D. Ark.), transfers were made to limited partnerships, and discounts were taken for lack of control and lack of marketability. The District Court held that the value of the partnership interests retained by the decedent should reflect a 41% discount for lack of control and lack of marketability. The court rejected the IRS argument that the transfer was without consideration, noting that a bona fide sale occurs where a transfer is made in good faith with “some potential benefit other than the potential estate tax advantages that might result from holding assets in partnership form.”

III.    Annual Exclusion Gifts

In Barnett v. U.S., 104 AFTR 2d 2009-5143 (W.D. Pa.), the decedent executed a durable power of attorney in favor of his son, who then made 17 annual exclusion gifts. Twelve of the checks were given before the decedent’s death, but were cashed after his death. The power of attorney did not contain an express authorization to make gifts. The District Court agreed with the IRS that all of the checks written by the son were includible in the decedent’s estate since the son lacked authority to make gifts.

[Note: Under NY General Obligations Law §5-1501, which became effective on 9/1/09, a power of appointment may contain a “Statutory Major Gifts Rider.” This rider, which must be executed simultaneously with the power of attorney itself, authorizes the agent to make gifts. The individual executing the power may (but need not) also authorize the agent to make gifts to the agent himself.]

IV.     Estate Tax Deductions

In Estate of Williams, T.C. Memo 2009-5, the decedent left interests in a Coca Cola bottling plant to four charities and to the children of her father’s business partner. Litigation between the charities and the estate resulted in the each charities receiving an additional $6 million. The IRS initially issued a deficiency, arguing that the estate had undervalued the stock. After the IRS abandoned this argument, the estate sought a refund based on the additional $24 million in charitable distributions. The IRS denied the refund, reasoning that any increase in the charitable deduction was offset by an increase in the value of the gross estate. The estate argued, and the Tax Court agreed, that the shares were not part of the decedent’s estate since the stock had been constructively sold years earlier.

In Estate of Miller, T.C. Memo 2009-119, a QTIP trust had been created for the benefit of the surviving spouse. However, no income was ever distributed to the surviving spouse, and the trust reported income on its own fiduciary income tax return. Upon the death of the surviving spouse, her estate argued that trust assets should not be included in her gross estate since she had never received income from it. [IRC §2044(a) includes in a decedent’s gross estate the value of any property in which the decedent had a qualifying income interest for life.] The Tax Court held for the IRS, stating that §2044(a) applies to any property for which a deduction was allowed under §2056(b)(7).

In Estate of Charania, 133 T.C. No. 7 (2009), the decedent resided in Belgium at the time of his death. At that time, he owned 250,000 shares of Citigroup, Inc., which would be considered U.S. property for estate tax purposes. The decedent and his wife were both born in Uganda and were citizens of the United Kingdom.  The estate claimed that only one-half of the stock was includible in the decedent’s gross estate, because the shares were community property under Belgian law.

In a case of first impression, the Tax Court, applying English law and English conflicts-of-law rules, held that the stock was not community property, since (i) under the principle of “immutability,” propery acquired after a change in domicile is subject to the regime established before the change in domicile; and (ii) although Belgian law contains a provision that would have allowed the decedent and his spouse to change the marital property regime, the couple did not avail themselves of that election.

V.     Waiver of Penalties

In Estate of Lee, T.C. Memo 2009-84, relying on an attorney’s professional advice, the estate claimed a marital deduction for a spouse who had actually died 46 days before the decedent. The rationale for taking the marital deduction stemmed from the naïve belief that a provision in the predeceasing spouse’s will which provided that anyone who did not survive the testator by six months would be deemed to have predeceased the testator, justified the federal estate tax deduction.

Although the predeceasing spouse provision would be valid as against other takers under the will, the Tax Court articulated that that a will cannot presume survivorship sufficient to satisfy the marital deduction requirements (except where it is not possible to determine factually which spouse survived). Nevertheless, court chose to abate the accuracy-related penalties, stating that reliance on a tax professional may be justified if, under all the facts and circumstances, the reliance is reasonable and the taxpayer acted in good faith.

However, the Estate of Fuertes was not so fortunate with respect to the waiver of penalties. 2009 WL 3028823 (N.D. Tex. 2009). Twenty-seven days after the due date of the estate tax return, the attorney applied for an extension and made a tax payment of $2.2 million. The IRS denied the extension and imposed late filing and late payment penalties totaling $554,958.28. The court granted the IRS motion for summary judgment, noting that the taxpayer must show that the failure did not result from willful neglect. Reasonable cause does not exist where the taxpayer relies on a tax attorney to timely file a return, since that does not constitute reliance on the legal advice of a professional.

VI.       Executor Liability

In U.S. v. Guyton, Jr., 103 AFTR 2d 2009-2112, the District Court held the executor liable for unpaid taxes relating to gain from the sale of a chicken farm which was reported on the decedent’s final income tax return. Although the taxes for which the executor was held liable related to an interest which passed outside of the probate estate, the court reasoned that state law provided an adequate remedy between the executor and his brother, who had entered into a written agreement concerning the payment of taxes. Moreover, since the IRS was not a party to that agreement, it could not be bound by its terms.

VII.      Formula Disclaimers

The Eighth Circuit, in Estate of Christiansen, approved the use of formula disclaimers. __F.3d__, No. 08-3844, (11/13/09); 2009 WL 3789908, aff’g 130 T.C. 1 (2008). Helen Christiansen left her entire estate to her daughter, Christine, with a gift over to a charity to the extent Christine disclaimed her legacy. By reason of the difficulty in valuing limited partnership interests, Christine disclaimed that portion of the estate that exceeded $6.35 million, as finally determined for estate tax purposes.

Following IRS examination, the estate agreed to a higher value for the partnership interests. However, by reason of the disclaimer, this adjustment simply resulted in more property passing to the charity, with no increase in estate tax liability. The IRS objected to the formula disclaimer on public policy grounds, stating that fractional disclaimers provide a disincentive to audit. The Eighth Circuit, in upholding the validity of the disclaimer, lectured the IRS, remarking that “we note that the Commissioner’s role is not merely to maximize tax receipts and conduct litigation based on a calculus as to which cases will result in the greatest collection. Rather, the Commissioner’s role is to enforce the tax laws.”

Although “savings clauses” had since Com’r. v. Procter, 142 F.2d 824 (4th Cir.), cert. denied, 323 U.S. 756 (1944), rev’g and rem’g 2 TCM [CCH] 429 (1943) been held in extreme judicial disfavor on public policy grounds, carefully drawn defined value formula clauses have seen a remarkable rehabilitation. So much so that the Tax Court in Christiansen concluded that it “did not find it necessary to consider Procter, since the formula in question involved only the parties’ current estimates of value, and not values finally determined for gift or estate tax purposes.”

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2009 Decisions and Rulings Under IRC Section 1031

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I.         Acquisition of All Partnership Interests Takes Exchange Out of IRC § 1031(a)(2)(D)

PLR 200909008 concluded that an Exchange Accommodation Titleholder (“EAT”) may acquire a 50% partnership interest as replacement property for the taxpayer’s exchange where the taxpayer owns the other 50%. Although §1031(a)(2)(D) precludes the exchange of a partnership interest, under Rev. Rul. 99-6, the acquisition by a partner of all of the remaining interests of a partnership is treated as the acquisition of a pro rata share of the underlying property, rather than the acquisition of a partnership interest.

II. “Qualified Use” Requirement Relaxed Where Trust Funds LLC Which Engages in Swap

In PLR 200812012, under the terms of decedent’s will, Trust A was established to administer estate assets. The trust owned real property in various states which were held for investment. Pursuant to a termination plan formulated by the trustees, Trust A assets were contributed to an LLC. The issue raised was whether the LLC could thereafter engage in a like kind exchange. The IRS ruled favorably, noting that Trust A terminated involuntarily by its own terms after many years in existence. The ruling also noted that there was no change in beneficial ownership of the LLC, or the manner in which it holds or manages the replacement property. The ruling distinguished Rev. Rul. 77-337, which involved “voluntary transfers of properties pursuant to prearranged plans.”

III.  QI Status Not Affected By Conversion of S Corps to C Corps

In PLR 200908005, the IRS ruled that the conversion of three subchapter S corporations, which engaged in the business of acting as qualified intermediaries for like kind exchanges, to C corporations, would not be considered a change in the qualified intermediaries, despite the formation of three new taxpayer entities. The IRS reasoned that although the C corporation would no longer be a disregarded entity under federal tax law, the three entities would be the same for state law purposes, and there would be no change in the manner in which the corporations conducted business. This ruling leaves open the question of how the IRS would view the acquisitions of a bankrupt or insolvent qualified intermediary by another entity.

IV.  Acquisition of All Interestsin Partnership Results in Good Like Kind Exchange

In PLR 200807005, taxpayer, a limited partnership, intended to form a wholly-owned LLC which would be a disregarded entity for federal tax purposes. It would then acquire 100 percent of the interests of the partners in a partnership in a like kind exchange. After the exchange, the LLC would be a general partner and the taxpayer a limited partner in the partnership.

The ruling raised two issues: First, does the exchange qualify for nonrecognition under IRC § 1031?  The ruling answered this in the affirmative. Pursuant to Rev. Rul. 99-6, the partnership is considered to have terminated under IRC §708(b)(1)(A), and made a liquidating distribution of its real property assets to its partners, and the taxpayer is treated as having acquired those interests from the partners, rather than from the partnership, for federal tax purposes. Accordingly, the transaction is a like kind exchange, rather than an exchange of partnership interests.

The second issue raised was whether the taxpayer may hold the replacement property in a newly-created state law partnership that is disregarded for federal income tax purposes. Since the LLC is disregarded for tax purposes, and the taxpayer, who owns 100 percent of the partnership following the exchange, is considered as owning all of the real estate owned by the partnership, the ruling concluded that the taxpayer may hold the replacement property in a newly-created state law partnership that is disregarded for federal income tax purposes without violating the requirement of IRC § 1031 that replacement and relinquished property both must be held by the [same] taxpayer.

V.  Development Rights Are Real Property For Purposes of IRC § 1031

PLR 200901020 ruled that development rights qualified as real property for purposes of Section 1031. In the facts of the ruling, property owner contracted to sell (relinquish) certain parcels of property. The contract contained a put option, which entitled the seller to transfer some or all of its residential development rights under a phased development plan. If the option was exercised, the buyer was required to sell certain hotel development rights back to the seller. After determining that the development rights constituted real property under state law, the PLR then stated that the development rights would qualify as like kind property if the rights were in perpetuity, and were directly related to the taxpayer’s use and enjoyment of the underlying property. The ruling concluded that the taxpayer had met these criteria.

VI.  Leasehold Interests Are of “Like Kind” to other Leasehold Interests; Basis of Property in Multiple Property Exchanges

In PLR 200842019, the taxpayer exchanged an existing leasehold interest for a new lease. The ruling stated that a leasehold interest with permanent improvements is of like-kind to another leasehold interest with permanent improvements. Variations in value or desirability relate only to the “grade or quality” of the properties and not to their “kind or class.” Depreciable tangible personal property is of like kind to other depreciable tangible personal property in the same General Asset Class. In this case, all of the depreciable personal property to be exchanged, i.e., office furniture, fixtures and equipment, is in the same General Asset Class.

Treas. Regs. § 1.1031(k)-1(e)(1) provides that the transfer of relinquished property will not fail to qualify for nonrecognition under § 1031 merely because replacement property is not in existence or is being produced at the time the property is identified as replacement property. Treas. Regs. §1.1031(j)-1(c) sets forth the exclusive method of basis computation for properties received in multiple property exchanges. In such exchanges, the aggregate basis of properties received in each of the exchange groups is the aggregate adjusted basis of the properties transferred by the taxpayer within that exchange group, increased by the amount of gain recognized by the taxpayer with respect to that exchange group, with other adjustments. The resulting aggregate basis of each exchange group is allocated proportionately to each property received in the exchange group in accordance with its fair market value. Therefore, the basis of property received by the taxpayer will be determined on a property-by-property basis beginning by first ascertaining the basis of each property transferred in the exchange and adjusting the basis of each property in the manner provided in Treas. Regs. § 1.1031(j)-1(c). Even if no cash is received in an exchange involving multiple properties, it is possible that boot will be produced, because property acquired within an exchange group may be of less value than property relinquished within that exchange group.

VII. Properties Can Be of “Like Kind” Without Being of “Like Class”

In PLR 200912004, taxpayer operated a leasing business, in which the taxpayer purchases and sells vehicles as the leases terminate. The taxpayer implemented a like kind exchange program pursuant to which the taxpayer exchanges vehicles through a qualified intermediary under a master exchange agreement. The taxpayer proposes to combine into single exchange groups all of its cars, light-duty trucks and vehicles that share characteristics of both cars and light duty trucks, arguing that all such vehicles are of like kind under Section 1031.

Ruling favorably, the IRS noted that although the taxpayer’s cars and light duty trucks are not of like class, Treas. Regs. § 1.1031(a)-2(a) provides that an exchange of properties that are not of like class may qualify for non-recognition under Section 1031 if they are of like kind. Moreover, Treas. Regs. § 1.1031(a)(2(a) provides that “in determining whether exchange properties are [of] a like kind no inference is to be drawn from the fact that the properties are not of a like class.” Thus, properties can be in different asset classes and still be of like kind.

VIII.   IRS Finds Trademarks Qualify as Like Kind Property

The IRS recently reversed its long held position that intangibles such as trademarks, trade names, mastheads, and customer based intangibles could not qualify as like kind property under Section 1031. Chief Counsel Advisory (CCA) 20091106 stated that these intangibles may qualify as like kind property provided they can be separately valued apart from a business’s goodwill, and that except in “rare or unusual circumstances” they should be valued apart from goodwill. Even so, the “nature and character” requirements of Treas. Regs. § 1.1031(a)(2)(c)(1) must still be met. Thus, not all trademarks, trade names and mastheads are of like kind to other trademarks, trade names and mastheads.

CCA 20091106 opens up new planning opportunities for business owners seeking to swap similar businesses. Business owners may now defer gain not only with like-kind or like-class tangible assets, but also with like-kind non-goodwill intangibles disposed of in an exchange.  Utilizing a “reverse exchange,” taxpayers may “park” non-goodwill intangibles with an EAT, and use the parked property as part of a like-kind exchange within 180 days.

IX.  Ninth Circuit Affirms in Teruya

The Ninth Circuit upheld the Tax Court’s decision in Teruya. No. 05-73779 (9/8/09). The Court of Appeals found that Teruya had “decreased their investment in real property by approximately $13.4 million, and increased their cash position by the same amount.” Therefore, Teruya had effectively “cashed out” of its investment. Noting that Teruya could have achieved the same property disposition through “far simpler means,” the court concluded that the transactions “took their peculiar structure for no purpose except to avoid § 1031(f). The presence of the QI, which ensured that Teruya was “technically exchanging properties with the qualified intermediary . . . served no purpose besides rendering simple – but tax disadvantageous – transactions more complex in order to avoid § 1031(f)’s restrictions.” The exception in § 1031(f)(2)(C) was inapplicable since “the improper avoidance of federal income tax was one of the principal purposes.”

X.  Ocumulgee Fields Further Restricts Exchanges Between Related Parties

In Ocumulgee Fields v. Com’r., T.C. No. 6 (2009), the taxpayer transferred appreciated property to a qualified intermediary under an exchange agreement, whereupon the QI sold the same property to an unrelated party and used the sale proceeds to purchase like kind property from a related person that was transferred back to the taxpayer to complete the exchange. The IRS assessed a deficiency, arguing that the exchange was part of a series of transactions designed to avoid IRC § 1031(f) and that the taxpayer had not established the “lack of tax avoidance” exception under § 1031(f)(2)(C). Citing Teruya Bros., Ltd., the Tax Court agreed with the IRS, noting that the immediate tax consequence of the exchange would have been (i) to reduce taxable gain by $1.8 million, and (ii) to substitute a 15% tax rate for a 34% tax rate.

After Ocumulgee, and the Ninth Circuit decision in Teruya, it may be difficult to find a more likely than not basis to proceed with an exchange involving a related party in instances where the related party already owned the replacement property. The Tax Court came perilously close to holding that basis shifting virtually precludes, as a matter of law, the absence of a principal purpose of tax avoidance.

XI. Related Party Rules Not Violated Where Equalizing Transfers of TIC Interests Made By Trust Beneficiaries

In PLR 20091027, the taxpayer, the taxpayer’s sibling, and a trust were tenants in common of real property. The trustees of the trust wished to sell their interest in the real property. To increase the marketability of the interests sold, the three owners each agreed to exchange their undivided 1/3 interest in the property for 100 percent fee simple interests in the same property. The proposed division would split the property into three parcels of equal value.

The taxpayer sought a ruling regarding the applicability of IRC § 1031(f) to the proposed exchange. The ruling held that while the taxpayer and the taxpayer’s sibling were related, neither intended to sell their property within two years. Furthermore, the taxpayer was not related to the trust within the meaning of IRC § 1031(f)(3); (i.e., the trust did not bear a relationship to the taxpayer described in IRC §267(b) or §707(b)(1)). Accordingly, the ruling concluded that with respect to the taxpayer and the trust, there was no exchange between related persons for purposes of IRC §1031(f).

XI. IRS Counsel Opines that Same Property May be Relinquished for Reverse Exchange and for Forward Deferred Exchange

In CCA 200836024 the taxpayer, pursuant to Rev. Proc. 2000-37, first structured an “exchange last” reverse exchange. In the reverse exchange, Greenacre was acquired by the EAT as replacement property, and parked until the taxpayer identified property to be relinquished. Thirty-three days after Greenacre was acquired by the EAT, the taxpayer identified three properties to potentially serve as relinquished property for Greenacre. Redacre was one of those properties. On the 180th day following the EAT’s acquisition of Greenacre, Redacre was relinquished in the reverse exchange, and that exchange was unwound. However, since the value of Redacre far exceeded the value of Greenacre, the taxpayer structured a second like kind exchange to defer the gain that remained after the exchange of Redacre for Greenacre. Accordingly, 42 days after the sale of Redacre to cash buyer, the taxpayer identified three additional properties intended to be replacement properties for the relinquishment of Redacre in a deferred exchange.

The issue was whether the taxpayer could utilize Redacre both as the relinquished property in a reverse exchange, and also as the relinquished property in a deferred exchange. The answer was yes. Reasoning that the taxpayer had complied with identification requirements for both a reverse and a deferred exchange, the advisory concluded that the taxpayer could properly engage in both a reverse exchange and a deferred exchange with respect to the same relinquished property.

The CCA further noted that Rev. Proc. 2000-37 anticipated the use of a qualified intermediary in a reverse exchange. The advice also cited Starker v. U.S., 602 F.2d 1341 (9th Cir. 1979) (transfers need not occur simultaneously); Coastal Terminals, Inc., v. U.S., 320 F.2d 333 (4th Cir. 1963) (tax consequences depend on what the parties intended and accomplished rather than the separate steps); and Alderson v. Com’r., 317 F.2d 790 (9th Cir. 1963) (parties can amend a previously executed sales agreement to provide for an exchange), for the proposition that courts have long permitted taxpayers “significant latitude” in structuring like-kind exchanges.

XII. IRS Declines to Regulate Qualified Intermediaries

Consolidation of qualified intermediaries has raised concerns regarding transfers of QI accounts during exchanges.  There continues to be concern with respect to QI insolvencies as a result of several well-publicized failures, e.g., LandAmerica, November 2008.  The Federation of Exchange Accommodators (FEA) has asked the Federal Trade Commission (FTC) and the IRS to regulate qualified intermediaries.  Both have declined.  Nevada and California do regulate qualified intermediaries. Under California law, the QI is required to use a qualified escrow or trust, or maintain a fidelity bond or post securities, cash or a letter of credit in the amount of $1 million. The QI must also have an errors and omissions insurance policy. Exchange facilitators must meet the prudent investor standard, and cannot commingle exchange funds. A violation of the California law creates a civil cause of action.

XIII.  Build-to-Suit Rules Relaxed in PLR

In PLR 200901004, the IRS ruled favorable with respect to an exchange where taxpayer, engaged in the business of processing minerals in Old Facility, assigned easements to its wholly-owned LLC, which would then construct New Facility also for the purpose of processing minerals. The LLC would acquire funds for project financing through a syndicate of third party lenders, and the financing would be secured by the New Facility. Lenders would have the right to foreclose on the New Facility, including the rights of the LLC under the assigned easements. The ruling cautioned that the proposed exchange between the LLC and the taxpayer, though qualifying under Section 1031, constituted an exchange of multiple properties, both tangible and intangible, pursuant to Treas. Regs. § 1.1031(j)-1. This necessitated a property-by-property comparison to determine the extent of any boot present in the exchange.

XIV.  Ruling Provides Flexibility in Two-Party TIC Exchanges

In three recent rulings, PLRs 200826005, 200829012 and 200829013, the IRS ruled that two 50% undivided fractional interests in real property did not constitute an interest in a business entity for purposes of qualification as eligible replacement property in a §1031 exchange. The rulings provide flexibility to two-party 50% tenancy-in-common ownership structures with regard to qualification as eligible replacement property. In approving a two-party 50% undivided interest structure for purposes of qualifying §1031 exchanges, the ruling modified several conditions specified in Rev. Proc. 2002-22:

¶  The Agreements between the two co-owners required the co-owners to invoke the buy-sell procedure prior to exercising their right to partition the property. Since Rev. Proc. 2002-22 provides that each co-owner must have the right to partition, the PLRs construed this requirement with great latitude. Although Rev. Proc. 2002-22 provides that each co-owner may encumber their property without the approval of any person, the Agreement in question allowed each co-owner the right to approve encumbrances. The IRS reasoned that since there are only two 50% owners, the restriction on the right of a co-owner to engage in activities that could significantly diminish the value of the other 50% interest without the approval of the other co-owner was consistent with the requirement that each co-owner have the right to approve an arrangement that would create a lien on the property.

¶   The PLRs modified a requirement within Rev. Proc. 2002-22 regarding proportionate payment of debt. While Rev. Proc. 2002-22 provides that each co-owner must share in any indebtedness secured by a blanket lien in proportion to their own indebtedness, the PLR approved an arrangement whereby an owner who paid more than 50% would have the right to be indemnified by the other co-owner. The Agreement provides a mechanism whereby the co-owners could pay an amount that deviates from their proportionate share of debt.

¶   While Rev. Proc. 2002-22 limits co-owners’ activities to those customarily performed in connection with the maintenance and repair of rental real property, the PLRs approved a provision allowing co-owners to lease the property to an affiliated entity. In each PLR, the properties were leased to an affiliate of one of the co-owners who conducts a business unrelated to the management and leasing of the property.

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Estate Planning Synopsis

ESTATE PLANNING SYNOPSIS

1.    Estate Planning

a.    The level of sophistication of estate plans varies with the size and complexity of an individual’s estate. A carefully drafted Will or revocable inter vivos trust is the starting point for many estate plans.

b.    The following relatively simple documents may be important in the event of disability or incapacity: the health care proxy appoints an agent to make medical decisions in the event of incapacity. The living will states whether or not extraordinary means are to be used to keep one alive. The durable power of attorney, for financial transactions, survives incapacity, so that guardianship can be avoided. The durable power of attorney can be used to place assets into an existing inter vivos trust in the event of the incapacity of the grantor.

c.    Everybody needs a will.  A will tells the world exactly how you want your assets divided and where you want your assets distributed when you die. If you die without a will, the law will decide how your assets should be distributed. This is not the main reason to draft a will, as your assets will be divided amongst your immediate family according to intestate law.  However, the law does not take into consideration the tax savings elements that a will can accomplish.

i.    Federal Estate Tax.   If you plan carefully, you can substantially reduce if not eliminate estate taxes.  Both the estate tax and family estate planning objectives of the decedent can be accomplished with a will.

ii.    Old Wills.  Your existing Will should be reviewed to determine whether it accurately reflects your present testamentary objectives.

iii.    Exemption amount increased to $3.5 million.    In 2009, the federal estate tax exemption amount will be increase to $3.5 million.  In 2010, the estate tax will be eliminated for that year.  Obama has said that he will most likely freeze the estate tax at $3.5 million.  The exemption amount was at $600,000 not too long ago.

(1)    Many wills drafted prior to EGTRRA employ “formula” clauses eliminating estate tax on the death of the first spouse by creating a “credit shelter” trust funded with assets equal to the unused applicable exclusion amount (AEA), and then distributing the remainder of the residuary estate to the surviving spouse outright or in a marital deduction trust, such as a QTIP. The combination of the unified credit and marital deduction result in no tax at the first death. Anyone, including the surviving spouse, may be a beneficiary of the credit shelter trust, but to qualify for the QTIP marital deduction, only the surviving spouse may possess rights to income or principal. In fact, the surviving spouse must alone have the right to receive all income from the QTIP trust, paid at least annually, and no other person may be a beneficiary of that trust during the surviving spouse’s life. With the AEA reaching new levels far exceeding previous amounts, and with New York, retaining lower threshold levels for the imposition of estate tax, older formula clauses may produce unintended results.  The danger exists that by funding the nonmarital (credit shelter) trust with the maximum amount that can be shielded by the AEA, the surviving spouse might be unintentionally disinherited. Particularly in cases where the estate is less than $4 million and the surviving spouse is not granted distribution rights to the nonmarital trust, consideration should be given to capping the formula clause allocation to the nonmarital trust at a level substantially below the AEA, perhaps at an amount no greater than the amount that can pass free of New York estate tax.

(2)    Nevertheless, by capping the nonmarital share and increasing the marital share, a new problem arises: The estate of the surviving spouse might become subject to estate taxes. Fortunately, this problem can be avoided by funding a second nonmarital trust with the excess of the applicable exclusion amount over the cap placed on the first nonmarital trust. The surviving spouse could even be the sole beneficiary of this trust, the assets of which would remain outside of her taxable estate since no QTIP election will have been made. To illustrate, assume decedent dies in 2009 with a taxable estate of $5 million at a time when the AEA is $3.5 million. Nonmarital Trust #1 is funded with $1 million, the maximum amount that can pass free of New York estate tax. Nonmarital Trust #2 with $2.5 million, and the QTIP Trust with $1.5 million. Nonmarital Trust #1 and Nonmarital Trust #2 make full use of the AEA. The surviving spouse is granted the same distribution rights to Nonmarital Trust #2 as she is to the QTIP. Nonmarital Trust #2 will not, however, be included in her taxable estate because no QTIP election will have been made.

(3)    Now consider New York estate tax consequences: New York’s applicable exclusion amount is $1 million, frozen at pre-EGTRRA levels. Nonmarital Trust #1 therefore makes full use of New York’s excludible amount. Does this mean that Nonmarital Trust #2 will attract New York estate tax?  Not necessarily. Even though no federal QTIP election will be made for Nonmarital Trust #2, since New York has “decoupled” its estate tax from the federal estate tax regime, that trust might still qualify for the unlimited marital deduction for New York state estate tax purposes. If this strategy succeeds, Nonmarital Trust #2 would be includible in the surviving spouse’s estate for New York, but not for federal, estate tax purposes.

(4)    This plan would (i) eliminate New York (and federal) estate tax completely on the death of the first spouse without overfunding the federal QTIP which will be subject to federal estate tax at the death of the surviving spouse; while (ii) providing maximum benefits to the surviving spouse. Even if no New York marital deduction is allowed for estate tax purposes, the assets in Nonmarital Trust #2 — a trust over which the surviving spouse will have substantial rights — will not be included in her federal taxable estate, because no QTIP election will have been made with respect to it.

iv.    Unlimited Marital Deduction

(1)    In general, the U.S. gift tax and estate tax laws permit unlimited tax-free transfers of property between spouses if the transferee spouse (i.e., the spouse receiving property) is a U.S. citizen. This “marital deduction” often is said to reflect the view that a husband and wife represent a single economic unit, and only transfers from that unit to third parties (e.g., children) should be subject to gift and estate tax.

(2)    At death, if the surviving spouse is not a U.S. citizen, the transfer will not qualify for the unlimited marital deduction unless it passes to a qualified domestic trust.  Thus, when one or both spouses in a married couple are not U.S. citizens, special planning may be required to avoid adverse tax consequences for transfers during lifetime or at death.  Although widely criticized, this rule is based on a concern that the non-citizen spouse might move to another country and thereafter transfer property he or she received tax-free without being subject to U.S. gift and estate taxes.

(3)    You may leave an unlimited amount of money to your spouse tax-free, but this is not always the best tactic.  By leaving all your assets to your spouse, you don’t make use of your estate tax exemption.  Instead, the size of your surviving spouse’s estate is increased and when the surviving spouse dies, your children are likely to pay more in estate taxes.

(a)    HYPO: A husband and wife owning less than $7 million in assets will not pay estate taxes as they can both make use of their $3.5 million exemption amounts.

(b)    Yes, you can leave everything to your spouse and not pay any tax but one has to take into consideration what happens when the second spouse dies.

(4)    Wills providing for a testamentary QTIP trust might provide for an alternate disposition into another trust for the spouse or heirs if estate tax has been repealed at the testator’s death. Both revocable and irrevocable trusts might be drafted to include a power vested in an independent trustee to change the terms of the trust while the grantor is alive to take into account the changes in the estate tax. The trustee of an irrevocable trust might be given authority to make greater distributions to the grantor. However, one must ensure that such greater powers do not cause trust assets to be included in the grantor’s estate under IRC § 2036.

v.    Avoidance of estate tax in the surviving spouse’s estate is also  important. The decedent’s Will may direct that the proceeds of his policy be held in trust, with the surviving spouse allowed an income interest in trust assets. If a QTIP election were made by the decedent’s executor, or if the surviving spouse were granted either a power to invade the corpus of the trust or a general power of appointment, inclusion in her estate would be unavoidable. Conversely, if no marital deduction were claimed by the estate of the decedent, and the surviving spouse’s right to invade the trust corpus were limited by an “ascertainable standard” for her health, education, support, or maintenance, inclusion in her estate could be avoided. Moreover, the surviving spouse could be given a noncumulative yearly right to withdraw the greater of 5 percent of the balance of the proceeds, or $5,000, without risking inclusion in her estate.

vi.    Alternatives to a Will:    Wills eventually become public after your death:
(1)    Revocable living trusts.  Trusts will not save you anything in estate taxes.  Trusts are used to avoid probate.
(2)    Gifting assets before your death. $1,000,000
(3)    Joint tenancy.  Joint tenancy is a method of holding title to property when two or more persons own property together, but the final survivor will be wind up with the entire property.

2.    Comparison:  Will or Trust
a.    Transfer of assets
i.    Will: No transfer of assets required
ii.    Trust: Extensive transfers required
b.    Maintenance
i.    Will:    None
ii.    Trust:    Extensive maintenance; all activities must be conducted in name of trust
c.    Planning for Disability
i.    Will:    Offers little; however, can be used in conjunction with Durable Power of attorney
ii.    Trust:    Offers considerable flexibility; a living trust can be established with a co-trustee assuming primary responsibility for the management of assets.
d.    Present Costs
i.    Will:    Drafting of Will
ii.    Trust:    Drafting of Trust, transfer of assets into trust
e.    Need for other Legal Documents
i.    Will:      Generally, trust not necessary
ii.    Trust:    Pour-over will necessary
f.    Confidentiality
i.    Will:    Probate is public
(1)    In Terrorem clause probably ineffective
ii.    Trust:    Although higher degree of confidentiality, trust document could nevertheless become public
g.    Legal Fees at Death
i.    Will:     Probate Fees
(1)    Nonprobate assets include:
(a)    jointly held home
(b)    insurance with designated beneficiaries
ii.    Trust:    Administration Fees
h.    Administration of Estate
i.    Will:    Probate can be time consuming
ii.    Trust:    Estate can be administered more quickly
i.    Will Contests
i.    Wills:    Will can be challenged
ii.    Trusts: Can also be challenged, but since in existence before  death, less of a likelihood that it will be challenged.
(1)    Trust may require greater mental facilities
(2)    In that respect, may be easier to upset trust.
j.    Governmental Assistance
i.    Will:     Can create testamentary trust which gives spouse benefit of assets while still qualifying for government assistance
ii.    Trust:   Testamentary trusts created by revocable trusts will not be excluded for purposes of determining eligibility for governmental assistance.

3.    Annual Gift Tax Exclusion

a.    In 2009, you may give up to $13,000 a year to an individual (or $26,000 if you’re married).  You may also pay an unlimited amount of medical and education bills for someone if you pay these expenses directly to the institutions where they were incurred.  You do not need to file a gift tax return for these gifts.

4.    LLCs for Estate Planning

a.    To accomplish the objectives of wealth transfer, business succession, and asset protection, the LLC has emerged as the clear entity of choice. The LLC can be used to shift income to lower bracket taxpayers, to shift wealth while leveraging the unified credit, and to effectively protect assets from claims of creditors. Favorable basis rules make the LLC an extremely attractive vehicle for real estate. The LLC operating agreement can provide for succession of a family business after the death of a member.

b.    Installment sales of assets to grantor trusts indirectly exploit income tax provisions enacted to prevent income shifting at a time when trust income tax rates were much lower than individual tax rates. Specifically, the technique  capitalizes on different definitions of “transfer” for transfer tax and grantor trust income tax purposes. The resulting trusts are termed “defective” because the different definitions of “transfer” result in a serendipitous divergence in income and transfer tax treatment when assets are sold by the grantor to his own grantor trust.

c.    Overview of Asset Sale.    For income tax purposes, after an asset sale has occurred, the grantor trust holds property on which the grantor continues to report income tax.  However, the grantor is no longer considered as owning the asset for transfer tax purposes, and the trust assets, as well as the appreciation thereon, will be outside of the grantor’s taxable estate. As a result of this odd juxtaposition of income and transfer tax rules, the grantor is taxed on trust income but will have depleted his estate of the value of the assets for transfer tax purposes.

i.    To illustrate the mechanics, assume the grantor sells property worth $5 million to a trust in exchange for a $5 million promissory note, the terms of which provide for adequate interest payable over 20 years, and one balloon payment of principal after 20 years. If the trust is drafted so that the grantor retains certain powers, income will continue to be taxed to the grantor, even though for transfer tax purposes the grantor will be considered to have parted with the property.   This may over time reduce transfer taxes since the grantor is in effect making a tax-free gift to trust beneficiaries of money needed to pay the income tax liability of the trust.  Assume that the grantor has sold a family business worth $5 million to the trust, and that each year the business is expected to generate approximately $100,000 in profit.  Assume further that the trust is the owner of the business for transfer tax purposes. With the grantor trust in place, the grantor will pay income tax on the $100,000 of yearly income earned by the business. If the business had instead been given outright to the children, they would have been required to pay income taxes on the profits of the business.

d.    The result of the sale to the defective grantor trust (“IDT” or “trust”) is that the income tax liability of the profits generated by the business remains the legal responsibility of the grantor, while at the same time the grantor has parted with ownership of the business for transfer tax purposes. A “freeze” of the estate tax value has been achieved, since future appreciation in the business will be outside of the grantor’s taxable estate. Nonetheless, the grantor will remain liable for the income tax liabilities of the business, and no distributions will be required from the trust to pay income taxes on business profits. This will result in accelerated growth of trust assets.

i.    Achieving grantor trust status requires careful drafting of the trust agreement so that certain powers are retained by the grantor.   For as long as grantor trust status continues, trust income is taxed to the grantor. A corollary of the grantor trust rules would logically provide that no taxable event occurs on the sale of assets to the grantor trust because the grantor has presumably made a sale to himself of trust assets. Basically, the grantor can sell appreciated assets to the grantor trust, effect a complete transfer and freeze for estate tax purposes, and yet trigger no capital gains tax on the transfer of the appreciated business into the trust.

e.    The Note.    Consideration received by the grantor in exchange for assets sold to the IDT may be either cash or a note. If a  business is sold to the trust, it is unlikely that the business would have sufficient liquid assets to satisfy the sales price. Furthermore, paying cash would tend to defeat the purpose of the trust, which is to reduce the size of the grantor’s estate. Therefore, the most practical consideration would be a  promissory note payable over a fairly long term, perhaps 20 years, with interest-only payments in the early years, and a balloon payment of principal at the end.  This arrangement would also minimize the value of the business that “leaks” back into the grantor’s estate. For business reasons, and also to underscore the bona fides of the arrangement, the grantor could require the trust to secure the promissory note by pledging the trust assets.

i.    The note issued in exchange for the assets must bear interest at a rate determined under § 7872, which references the applicable federal rate (AFR) under §1274.   In contrast, a qualified annuity interest such as a GRAT must bear interest at a rate equal to 120 percent of the AFR. A consequence of this disparity is that property transferred to a GRAT must appreciate at a greater rate than property held by an IDT to achieve comparable transfer tax savings. As with a GRAT, if the assets fail to appreciate at the rate provided for in the note, the IDT would be required to “subsidize” payments by invading the principal of the trust. While no taxable event occurs when the grantor sells assets to the IDT in exchange for the note, if grantor trust status were to terminate during the term of the note, the trust would no longer be taxed as a grantor trust. This would result in the immediate gain recognition to the grantor, who would be required to pay tax on the unrealized appreciation of the assets previously sold to the trust.

f.    Consequences of Transferred Basis.    Note that for purposes of calculating realized gain, the trust will be required substitute the grantor’s basis:  Even though the assets were “purchased” by the trust, no cost basis under § 1012 is allowed since no gain will have been recognized by the IDT in the earlier asset sale. Another situation where gain will be triggered is where the trust sells appreciated trust assets to an outsider. One way of mitigating this possibility would be for the grantor to avoid initially selling appreciated assets to the trust. If this is not possible, the grantor could also substitute higher basis assets of equal value during the term of the trust, as discussed below.

i.    Care should be exercised in selling highly appreciated assets to the grantor trust for another reason as well:  if the grantor were to die during the trust term, the note would be included in the grantor’s estate at fair market value. However, the assets which were sold to the trust would not receive the benefit of a step-up in basis pursuant to § 1014(a). Any gift tax savings occasioned by the transfer of assets could be negated by the failure of the trust to receive an increase in basis. To avoid this result, the trust might either (i) authorize the grantor to substitute higher basis assets of equal value during his lifetime; or (ii) make payments on the note with appreciated assets. [Note that if the grantor received appreciated assets in payment of the note, those assets would be included in the grantor’s estate, if not disposed of earlier. However, they would at least be entitled to a step-up in basis in the grantor’s estate pursuant to § 1014.]

g.    As noted above, since the assets are being transferred to the grantor trust in a bona fide sale, those assets should be excluded from the grantor’s taxable estate. However, since the grantor is receiving a promissory note in exchange for the assets, the IRS could take the position that under § 2036, the grantor has retained an interest in the assets which require inclusion of those assets in the grantor’s estate.7 In order to minimize the chance of the IRS successfully invoking this argument, the trust should be funded in advance with assets worth at least 10 percent as much as the assets which are to be sold to the IDT in exchange for the promissory note.

i.    In meeting the 10 percent threshold, the grantor himself should make a gift of these assets so that after the sale in exchange for the promissory note, the grantor will be treated as the owner of all trust assets.

h.    Choice of Trustee.    Trustee designations should also be considered: Ideally, the grantor should not be the trustee of an IDT, as this would risk inclusion in the grantor’s estate, especially if the grantor could make discretionary distributions to himself. If discretion to make distributions to the grantor is vested in a trustee other than the grantor, then the risk of adverse estate tax consequences is reduced. The risk is reduced still further if the grantor is given no right to receive even discretionary distributions from the trust. If the grantor insists on being the trustee of the IDT, then the grantor’s powers should be limited to administrative powers, such as the power to allocate receipts and disbursements between income and principal. The grantor may also retain the power to distribute income or principal to trust beneficiaries, provided the power is limited by a definite external standard.

i.    The grantor as trustee should not retain the right to use trust assets to satisfy his legal support obligations, as this would result in inclusion under §2036. However, if the power to satisfy the grantor’s support obligations with trust assets is within the discretion of an independent trustee, inclusion in the grantor’s estate should not result. However, if the grantor retains the right to replace the trustee, then the trustee is likely not independent, and inclusion would probably result. Note that despite the numerous prohibitions against the grantor being named trustee, the grantor’s spouse may be named a beneficiary or trustee of the trust without risking inclusion in the grantor’s estate.

i.    Death of Grantor.    The following events occur upon the death of the grantor: (i) the IDT loses its grantor trust status; and (ii) presumably, assets in the IDT would be treated as passing from the grantor to the (now irrevocable) trust without a sale, in much the same fashion that assets pass from a revocable living trust to beneficiaries. For reasons similar to those discussed above with respect to sales of appreciated trust assets, the basis of trust assets would not be stepped-up pursuant to §1014(a) on the death of the grantor, because the assets will not be included in the grantor’s estate. This is in sharp contrast to the situation obtaining with a GRAT, where the death of the grantor prior to the expiration of the trust term results in the entire amount of the appreciated trust assets being included in the grantor’s estate.

i.    Tax consequences of the unpaid balance of the note must also be considered when the grantor dies. Since the asset sale is ignored for income tax purposes, the balance due on the note would not constitute income in respect of a decedent.. The remaining balance of the note would however be included in the grantor’s estate and would acquire a basis equal to the value included in the estate.

j.    LLC Combined With IDT Asset Sale.    By combining the LLC form with asset sales to grantor trusts, it may be possible to achieve even more significant estate and income tax savings. LLC membership interests are entitled to minority discounts since the interests are subject to significant restrictions on transfer and management rights. If the value of the LLC membership interest transferred to the IDT is discounted for lack of marketability and lack of control, the value of that interest will be less than a proportionate part of the underlying assets.  Consequently, in the case of an asset sale to the IDT, the sale price will be less than if the assets had been directly sold to the IDT.

i.    To illustrate, assume the following events: (1) parent transfers real estate worth $1 million to a newly formed LLC of which parent is the Manager; (2) parent gives 10 percent  membership interests to each of two children; (3) parent gives a 10 percent  membership interest to a newly-formed grantor trust; and after a reasonable period of time (4) parent sells a 50 percent membership interest in the LLC to the grantor trust for fair market value. After the dust settles, parent will own a 20 percent interest in the LLC outright, the children will each will own a 10 percent interest, and the trust will own a 50 percent interest in the LLC.

(1)    In determining the FMV of the LLC interest sold to the trust, parent engages the services of a professional valuation discount appraiser and a real estate appraiser. It is determined that the value of the real estate is to be discounted by 50 percent after application of the lack of control and lack of marketability discounts. Therefore, the 50 percent  membership interest is sold to the trust for $250,000 (i.e., $500,000 x .5).  Parent agrees to accept a promissory note bearing interest at the rate of 6 percent, pursuant to § 1274, or $15,000 per year, with a balloon payment of principal at the end of the promissory note’s 15-year term.

(2)    If the underlying business appreciates at a yearly rate of 10 percent, the value of the underlying assets purchased by the trust in exchange for the promissory note would increase by $50,000 in the first year (i.e., $500,000 x .10). Had the LLC membership interests not been discounted, the real estate would have commanded a purchase price by the IDT of $500,000, and the required yearly interest payments would have instead been $60,000 (i.e., $500,000 x .06). By discounting the property purchased by the IDT to reflect minority discounts, the required interest payments to parent have been reduced from $30,000 to $15,000. If the underlying assets grow at a rate of 10 percent, then 70 percent  of the growth (i.e., $35,000/$50,000) can remain in the trust. It is apparent that more value can be transferred to family members if the property purchased by IDT in exchange for the promissory note can be discounted.

(3)    The LLC asset sale to the IDT would result in the following favorable tax and economic consequences: (i) $500,000 would be transferred out of the grantor’s estate for estate tax purposes; (ii) future appreciation on the $500,000 would be transferred permanently out of the estate; (iii) unlike the situation obtaining with a GRAT, the results in (i) and (ii) would not depend on the grantor surviving the trust term; (iv) since the promissory note could bear a lower rate of interest, fewer funds would be brought back into the grantor’s estate, resulting in a more perfect “freeze” for estate tax purposes; and (v) since the LLC assets are discounted, the purchase price by the trust would reflect that discount, making the effective yield of assets within the LLC even higher.

5.    New York State Estate Tax

a.    New York continues to impose an estate tax on estates over $1 million. Before EGTRRA, New York imposed a “pick up” estate tax on the maximum credit for state death tax allowed by IRC § 2011. However, EGTRRA has eliminated that credit in phases. Rather than lose estate tax revenue, some states, including New York have “decoupled” their tax codes from the federal code. New York has accomplished this objective by remaining linked to federal law as it existed before EGTRRA.

b.    Under pre-EGTRRA law, no federal estate tax would be imposed on an estate of $1 million. Since there would be no federal tax, New York would have nothing to “pick up”. However, a taxable estate of $1,093,755 would now incur tax of $38,452, which is 41% of the amount in excess of $1 million. If the taxable estate were greater than $1,093,755, the same $38,452 would be paid on the first $93,755 in excess of $1 million, but amounts in excess of $1,093,755 would be subject to tax at rates beginning at 6% and rising, for very large estates, to 16%.

6.    Trusts and Prenuptial Agreements

a.    The prenuptial agreement effectively protects against the vagaries of marital dissolution. However, even a well-drafted prenuptial agreement will not always succeed in fully accomplishing this objective. For example, the agreement will likely not prevent separate property from becoming marital property if assets are commingled. Nor is there any assurance that a prenuptial agreement will not be declared invalid in whole or in part if circumstances have changed during a long marriage, or if the equities of the case run against the party in whose favor enforcement of the prenuptial agreement would inure. Fortunately, the prenuptial agreement need not stand alone: Inherited family wealth and to a lesser extent assets acquired before marriage may be protected by a trust.

b.    Typically, a trust designed to protect family wealth would be created by a parent for the benefit of the either spouse. Unlike a prenup, the trust could be implemented at any time, even after marriage, and could exist without the knowledge other spouse. Trust distributions could be within the unreviewable discretion of the trustee, who might be the parent implementing the trust. Generally, inherited property, even that acquired during marriage, remains separate property.

c.    During the pendency of a divorce proceeding, the trustee could cease making distributions. Since the beneficiary could not force the trustee to make a distribution during the divorce, a fortiori the creditor-spouse could not. A creditor’s rights cannot exceed those of the debtor. (However, an exception might exist for court-ordered child support or alimony payments. A court might invade even a discretionary trust to satisfy these obligations.)

d.    Where a spouse has herself accumulated significant wealth before marriage, asset protection need also not stop with the prenup. Although NY EPTL § 7-3.1 has long provided that trusts created by the grantor for her own benefit which purport to shield trust assets from creditors are unenforceable, not all domestic jurisdictions continue to adhere to this common law view.

e.    A decade ago, one attempting to circumvent the EPTL prohibition against “self-settled” spendthrift trusts might have ventured to a remote venue with a tropical — or vaguely sinister — name. Today, one need venture no further than Delaware. This does not mean that a New York court would not look askance upon such a trust. Nonetheless, a New York court seeking to invade the trust might find it difficult to convince a Delaware court in whose jurisdiction the assets reside of the inapplicability of the Full Faith and Credit Clause.

7.    Step up in basis rules changed in 2010.   New basis rules to take effect in 2010 eliminate basis step-up in favor of a transferred basis regime. However, a $3 million basis increase will be allowed for property passing to a surviving spouse outright or in a QTIP trust; and a $1.3 million basis increase will be allowed for assets passing to any beneficiary, including the surviving spouse. Once these two permitted basis increases are exhausted, beneficiaries will receive assets without any basis increase. To avoid conflict among beneficiaries, the will could provide that assets should be allocated to the nonmarital share in a manner fairly reflecting the appreciation and depreciation in all assets available for allocation.

a.    Step up in basis- What is the rule now?  Why may not always be beneficial to put house in children’s name

8.    Like-Kind Exchanges

a.    Like-kind exchanges are an excellent estate planning, tool since at your death the property will receive a step-up in basis to fair market value.  Therefore, you could either continue to depreciate the property, or sell it without incurring any capital gains tax.

b.     IRC § 1031 provides for nonrecognition of gain or loss realized in a “like-kind” exchange of property held for productive use in a trade or business or for investment, provided the replacement property is held for the same purpose. The rationale for this venerated tax rule is that the new investment is merely a continuation of the old investment in another form. Through basis adjustments, the gain or loss is deferred until the property is liquidated. Instead of a cost basis, the transferor will take an exchanged basis. This substituted basis, depending on the circumstances, may not be favorable: For example, if appreciated real estate which has been fully depreciated is exchanged for new real estate, no depreciation deductions will be allowed with respect to the replacement property. If replacement property is worth more than exchanged property, additional consideration will be required to close. This nonqualifying property or “boot” (e.g., cash, unlike property, debt relief), will not cause the §1031 transaction to fail. Instead, realized gain will be recognized to the extent of this boot; the balance of realized gain will be deferred. (If the installment sales rules apply, boot gain may itself be deferred under § 453.)   Deferred exchanges may not be deferred beyond statutorily imposed dates. Thus, § 1031(a)(3) provides that replacement property must be identified within 45 days after the taxpayer transfers the relinquished property, and must be exchanged within 180 days thereafter, or by the due date of the taxpayer’s tax return (including extensions) for the tax year in which the transfer occurs, if earlier. Failure to meet either requirement results in a taxable sale.

i.    Although its requirements are technical, §1031 is not elective. Consequently, the nonrecognition of losses in an exchange that appears at first blush to require nonrecognition treatment may be undesirable, and could pose a trap for the unwary. However, by intentionally failing to comply with the statute’s technical rules, loss recognition should result. The Tax Court would likely be constrained to rule against the IRS if §1031 were not satisfied by reason of the replacement property not having been timely identified. Nevertheless, the taxpayer seeking to report losses should consider violating more than one statutory requirement, if possible. To defeat an IRS assertion that substance over form compels nonrecognition of losses, the taxpayer might gain advantage by violating both the continuity requirement (e.g., by deeding the property into a new entity immediately after the exchange) and the identification and exchange requirements.

ii.    What exactly constitutes “like-kind” property? Reg. §1.1031(a)-1(b) instructs that the term refers to the “nature or character of the property and not to its grade or quality within a class.” Real property exchanges have flourished because unimproved and improved real estate are considered to be of “like-kind,” provided the exchange involves the exchange of fee interests. (For this purpose, a leasehold interest of 30 or more years is identical to a fee interest.) Thus, real estate in the city for a farm or ranch qualifies (Reg. §1.1031(a)-1(c)), as does an apartment for vacant land plus golf course improvements (PLR 9428007).  Personal property, in contrast, must be nearly identical to qualify as like-kind. For example, a truck and an automobile are not like-kind, nor are bullion-type coins and numismatic coins, livestock of opposite sexes, a copyright on a song and a copyright on a novel, or even an antique desk and antique chair. Examples of personalty which meet the stringent definition include copyrights of novels, livestock of the same sex, antique automobiles, and baseball player contracts.

(1)     To illustrate the statute, assume M, Manhattanite,  wishes to exchange commercial real estate in Manhattan for commercial property in Hilton Head. Assume further that it would be difficult for M to locate an owner of commercial property in Hilton Head willing to swap island property with M in a direct exchange. L, Long Islander (who is himself indifferent to § 1031 treatment), has offered to buy M’s Manhattan property. One option would be for M to prevail upon L to purchase the Hilton Head property, and then engage in a like-kind exchange with L. In practice, L would likely be unwilling to purchase the Hilton Head property simply to accommodate M’s desire to acquire the Hilton Head property in a § 1031 exchange.

(2)    To facilitate an exchange in the event M cannot prevail upon L to purchase the Carolina property M may, pursuant to an agreement, transfer the property to an intermediary who (i) sells the property to L, (ii) purchases suitable exchange property in Hilton Head with the proceeds, and then (iii) transfers title in the newly purchased Hilton Head property back to M. For this “multiparty” deferred exchange to qualify under §1031, there must be no actual or constructive receipt of money or other property by M before the Hilton Head property is received. Otherwise, the transaction will be taxed as a sale.

iii.    Treas. Reg. §1.1031(k)-1 provides four safe harbors (which clarify and expand on decisional law) in structuring multiparty deferred exchange agreements which avoid actual or constructive receipt. The theme of each safe harbor is to preclude the transferor from receiving, pledging, borrowing or otherwise obtaining the benefits of money or other property before the end of the exchange period (except if no replacement property has been timely identified, in which case these rights may be invested in the transferor after the (lapsed) identification period, since §1031 would not apply.) If replacement property is timely identified, the transferor may then possess rights to receive, pledge, or borrow money upon the receipt of the replacement property, or even earlier, i.e., upon the occurrence of a written contingency that relates to the deferred exchange and is beyond the control of the transferor or other “disqualified persons,” excluding however the person obligated to transfer the replacement property. [Reg. §1.1031(k) defines “disqualified person” as a person who, within the 2-year period ending on the date of transfer of the relinquished property, acts as the taxpayer’s agent, employee, attorney, accountant, investment banker, broker or real estate agent.]

(1)    The first safe harbor provides that the transferor does not have actual or constructive receipt of money or other property before receipt of replacement property solely because the obligation of the other party to the transaction is or may be secured or guaranteed by (i) a mortgage, deed of trust or other security interest in property; (ii) a standby letter of credit (LC) that the transferor cannot draw upon except on default, or (iii) a guarantee of a third party. To revisit the previous illustration, L, desirous of the Manhattan property, agrees to purchase the Hilton Head property and then exchange it for the Manhattan property owned by M. Prior to transferring title to the Manhattan property, L is required to furnish a standby nonnegotiable and nontransferable LC which M may draw upon only in the event L does not deliver the Hilton Head property within 180 days after M relinquishes title to the Manhattan property. The LC satisfies the safe harbor rule and, assuming L delivers the Hilton Head property in a timely fashion, the transaction constitutes a like-kind exchange within respect to M.

(2)    The second safe harbor, similar to the first, relates to “qualified” escrow accounts, and provides that a transferor does not have actual or constructive receipt of money before the receipt of replacement property merely because the obligation of the other party to the transaction is or may be secured by cash or a cash equivalent held in a “qualified” escrow account. A qualified escrow account is one in which (i) neither the transferor nor other disqualified person is the escrow holder or trustee, and (ii) the escrow or trust agreement limits the transferor’s right to receive, pledge or borrow funds held in the escrow account or by the trustee.

(3)    The third safe harbor explores the  concept of qualified intermediary (recall the potential reluctance of L to purchase the Hilton Head property), and imposes three requirements to avoid constructive receipt: First, the intermediary can be neither the transferor nor the transferor’s agent, nor any person related to the transferor after application of the attribution rules found in §267(b) or §707(b); second, the agreement between the transferor and intermediary must expressly limit the former’s right to receive, pledge or borrow cash or property held by the intermediary; and third, the written agreement must obligate the intermediary to (i) acquire the relinquished property from the transferor; (ii) transfer the relinquished property to the transferee; (iii) acquire the replacement property; and (iv) transfer the replacement property to the transferor.

iv.    As alluded to earlier, the installment sales rules under § 453 will not necessarily hinder the application of §1031. Under those rules, the direct or indirect receipt of cash or cash equivalents is treated as receipt of payment. Reg. §1.1031(k) provides that a transferor is not deemed to have received an installment payment under a qualified escrow account or qualified trust arrangement, nor is the receipt of cash held in an escrow account by a qualified intermediary treated as a payment to the transferor under the rules, provided the transferor has a bona fide intent to enter into a deferred exchange at the beginning of the exchange period.

v.    The taxpayer holding real property may wish to exchange that property in a like-kind exchange and thereafter transfer the exchanged property into a corporation or LLC. Careful attention must be paid to the statute’s requirement of a continuation of business investment. Rev. Rul. 75-292 1975-2 opined that replacement property contributed to a corporation shortly after an exchange violates the requirement of continuity of investment and results in gain. The Tax Court however (Magneson, 81 TC 782, aff’d CA-9, 753 F2d 1490), distinguished this ruling and allowed an immediate contribution of property to a partnership. The taxpayer might permit the §1031 exchange to “age” before engaging in the contemplated transfer.

9.    Qualified Personal Residence Trust

a.    A QPRT is a powerful gifting tool that leverages the gift tax credit and freezes the appreciating residence at its current value.  The QPRT is an irrevocable trust that holds the residence for a terms of years.  In essence, a QPRT is formed when a grantor transfers a personal residence into a residence trust, and retains the right to live in the residence for a term of years. If the grantor dies before the end of the trust term, the trust assets are returned to the grantor’s estate, and pass under the terms of the grantor’s will.  However, if the grantor outlives the trust term, the residence passes to the named beneficiaries without any gift or estate tax event.

i.    A longer trust term will increase the value of the reserved term and decrease the initial taxable gift.

ii.    Any appreciation during the term of the trust would also have been diverted from the grantor’s estate.

10.    Life Insurance Trusts

a.    Life insurance proceeds are excludible from beneficiaries’ income under §101, provided the policy had not been transferred for valuable consideration. Proceeds from policies transferred in trust will also be excluded from the insured’s gross estate provided the insured (i) retained no incidents of ownership in the policy and (ii) survived three years after making the transfer. To ensure favorable estate tax consequences, the trust must also be both irrevocable and not amendable. It is therefore crucial that the insured understand the finality of decisions made when executing the trust.

b.    Even though the policy in trust may be excluded from the gross estate, proceeds can nevertheless be used to satisfy estate tax liabilities. However, the trust agreement must not obligate the trustee to assist in the payment of estate taxes. Thus, even though a major objective of an irrevocable life insurance trust may be to satisfy estate tax liabilities, the trust language must not mandatorily direct such payments. Language appearing to require the trust to pay estate taxes could result in estate tax inclusion under §2042 — regardless of whether the proceeds are so used.

c.    In order to accomplish the desired objective, the trust could authorize the trustee to purchase assets from, or make commercially reasonable loans to, the estate. Alternatively, the insurance proceeds might simply be distributable to beneficiaries who would ultimately bear the burden of estate taxes, as determined by the insured’s Will. The Will must be carefully coordinated with the Trust to accomplish that objective. Inconsistent language in the two instruments could result in harsh estate tax consequences.

d.    Life insurance trusts are flexible post-mortem vehicles for distributing income and principal to beneficiaries: If broad discretionary powers are granted to the trustee, principal may be distributed estate tax-free to children either when they reach a particular age, or earlier, if the trustee is given such discretion. The trust may also permit “sprinkling” income distributions to the surviving spouse, who may or may not require trust income or principal.

e.    To ameliorate the harsh estate tax consequences occasioned by the application the three-year inclusion rule, the trust might might direct that in such event insurance proceeds instead be payable to the insured’s estate. While this would negate provisions benefiting children, it would allow the Will (if so drafted) to claim a marital deduction which would at least keep the wolf at bay and result in exclusion from the gross estate.

f.    Premiums paid by the insured may qualify as annual exclusion gifts under the Crummey doctrine. The IRS has attempted to defeat Crummey powers where a contingent beneficiary had “no interest other than the withdrawal power”. However, the Tax Court in Kohlsatt (T.C. Memo 1997-212) rejected that position where “credible” reasons were offered by trust beneficiaries not to exercise withdrawal rights. Where the Crummey withdrawal right exceeds $5,000, the use of a “hanging” power may avoid the lapse which would cause a gift back into the trust by the Crummey beneficiary.

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Requirement of Filing Federal Gift Tax Return

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A.      Introduction

The requirement of filing a federal gift tax return arises when one has made a completed taxable gift. Incomplete gifts do not impose any gift tax filing requirement. Thus, the donor’s gift of a diamond ring would exemplify a completed gift. However, if the donor reserved the power to revest beneficial title in the ring to himself at a later date, the gift would be incomplete.

Many transfers in trust result in incomplete gifts. The donor who transfers property in trust with the direction to pay income to himself or to accumulate it in the discretion of the trustee, while retaining a testamentary power to appoint the remainder among his descendants, has made an incomplete gift. Treas. Reg. §25.2511-2.

The situation may arise where the taxpayer is unsure whether the gift is complete or incomplete. Treas. Reg. §301.6501(c)-1(f)(5) provides that adequate disclosure of a transfer that is reported as a completed gift will commence the running of the 3- year statute of limitations for assessment of gift tax, even if the transfer is ultimately determined to be an incomplete gift. However, in the converse situation, where a gift is reported as incomplete, but it is later determined to have been a completed gift, the result is less favorable: The period for assessing a gift tax will not commence to run until after a return has been filed reporting the completed gift.

Gifts qualifying for the annual exclusion, currently $12,000, are neither reported nor taxed. Gifts qualifying for the annual exclusion must be gifts of a present interest. Gifts consisting of a future interest, i.e., gifts in which the donee’s right to use, possess or enjoy the property will not commence until a future date, will not qualify for the annual exclusion. Treas. Reg. §25.2503-3. Transfers in trust that would otherwise constitute future interests may be converted to gifts of a present interest by the inclusion of what are termed “Crummey” withdrawal rights.

Certain transfers, which might otherwise be considered gifts, are by definition excluded from those transfers which require filing a gift tax return. Thus, under IRC §2503(e), the gift tax does not apply to “qualified transfers” made directly to (i) political organizations; (ii) “qualifying domestic or foreign educational organizations as tuition”; or (iii) medical care providers for the benefit of the donee.

Gifts to spouses may or may not require the filing of a gift tax return. Gifts qualifying for the marital deduction do not require the filing of a gift tax return, unless a QTIP election is contemplated, in which case the return must be filed in order to make the election. The gift of a terminable interest to a spouse also requires the filing of a gift tax return. The gift of a life estate, an estate for a specified number of years, or any other property interest that will terminate or fail after a period of time, will constitute a nondeductible terminable interest for which a gift tax return must be filed. IRC §2523.

Gifts to charities may require the filing of a gift tax return. If the donor’s only gifts during the year were to charities, no gift tax return need be filed. However, if the donor is required to report noncharitable gifts, gifts made to charitable entities must be reported on the return.

Some gifts which requiring reporting may not involve a situation where a “transfer” has occurred in its ordinary sense. Thus, even the exercise or release of a general power of appointment may constitute a taxable gift by the person releasing the power. IRC §2514(b). If a trust beneficiary releases a power to consume the principal of the trust, this would constitute a taxable gift.

Unlike the filing rules relating to income tax returns, there is no provision for the filing of joint gift tax returns. However, spouses may “split” gifts. By splitting a gift, both spouses are deemed to have made one-half of the taxable gift, regardless of which spouse actually transferred the property. To report a split gift, one spouse would file a gift tax return on which the non-filing spouse formally consents to the splitting of the gift by signing the return. Generally, the decision to split gifts applies to all made during the year. Treas. Reg. §25.2513-1(b). The executor or administrator of a deceased spouse, or the guardian of a legally incompetent spouse, may validly consent to split a gift. Treas. Reg. §25.2513-2(c). The consent to split gifts may not be made after the gift tax return has been filed.

If no gift tax is owed, a six month automatic extension sought for an filing income tax return on Form 4868 will also automatically extend the period for filing a Form 709 gift tax return until October 15th. However, if gift tax is owed, or if no income tax extension is sought, Form 8892 must be used.

Form 709 requires a statement disclosing the adjusted basis of gifted property. No actual calculation of basis is required. Without a disclosure of basis, the return may not be accepted as filed by the IRS. Treas. Reg. §1.1015-1(g) provides that persons making or receiving gifts should preserve and keep accessible a record of facts necessary to determine the cost of property and its fair market value as of the date of the gift.

B.      Gifts Requiring Disclosure

If the value of any item reported as a gift reflects any valuation discount, Form 709 requires that an explanation be attached to the return. The instructions specify that any gift reflecting, among others, a discount for lack of marketability, a minority interest, or a fractional interest in real estate, must be disclosed. When claiming a discount, the taxpayer must offer evidence that the discount is appropriate. Mere reliance on previous cases where discounts were upheld is insufficient.

Even if no gift tax is owed, the filing of Form 709 is crucial, as it commences the statute of limitations for revaluing the gift. Treas. Reg. §25.2504-2(b) provides that gifts “finally determined” cannot be revalued. The value of a gift is finally determined if (i) the three-year period under IRC §6501 to assess the gift tax has expired; and (ii) the gift has been “adequately disclosed” on the gift tax return.

For a gift to be adequately disclosed, the IRS must be apprised of the following information: (1) a description of the transferred property and any consideration received by the transferor; (2) the identity of, and the relationship between, the transferor and each transferee; (3) if the property is transferred in trust, the trust’s taxpayer identification number and a brief description of the terms of the trust, or in lieu of a brief description of the terms of the trust, a copy of the trust instrument; (4) a detailed description of the method used to determine the fair market value of the property transferred; and (5) a statement describing any position taken that is contrary to any proposed, temporary or final Treasury regulations or revenue rulings published at the time of the transfer.

A typical disclosure statement, for the sale of an LLC interest to a “defective” grantor trust, might contain the following language:  “The taxpayer sold 10 membership units in XYZ, LLC (the “LLC”) to the John Smith Irrevocable Trust dated June 15, 2006. The sales price was $3 million. The following adjustment clause was included in the Purchase Agreement:  ‘This transaction is intended to be an arm’s length transaction, free from donative intent. Accordingly, if, after the close of the transaction, the IRS determines that the fair market value of the membership units of the LLC is greater or less than the value determined by the appraisal used to establish the purchase price of the membership units, the purchase price will be adjusted to the fair market value as finally determined for Federal gift tax purposes by the IRS.’ A copy of the appraise of the membership units in XYZ, LLC is attached hereto as Exhibit 1.”

With respect to item (4) above, the detailed description should include (a) financial data (e.g., balance sheets utilized in determining the value of any interest); (b) any restrictions on the transferred property that were considered in determining the fair market value of the property; and (c) a description of any discounts (e.g., minority or fractional interests; lack of marketability) claimed in valuing the property.

The disclosure required by item (4) above may also be satisfied by an appraisal which meets the requirements of Treas. Reg. §301.6501(c)-1(f)(3). Such an appraisal must be prepared by an appraiser who satisfies all of the following requirements: (i) the appraiser is an expert who regularly performs appraisals; (ii) the appraiser possesses the expertise required to make appraisals of the type of property being valued; and (iii) the appraiser is not the donor or donee or a member of the family of the donor or donee.

The appraisal must contain the following information: (A) the date of the transfer, the date on which the transferred property was appraised, and the purpose of the appraisal; (B) a description of the property; (C) a description of the appraisal process employed; (D) a description of the assumptions, hypothetical conditions, and any limiting conditions that affect the analyses, opinions and conclusions; (E) the information considered in determining the appraised value; (F) the appraisal procedures followed; (G) the valuation method utilized; and (H) the specific basis for the valuation, such as specific comparable sales or transactions.

In some cases a decedent has failed to file required gift tax returns during his lifetime. In such a case, the executor, in computing the estate tax, must include any gifts in excess of the annual exclusion made by the decedent, or on behalf of the decedent under a power of attorney. The executor must make a “reasonable inquiry” as to such gifts, and the preparer should advise the executor of this responsibility. Instructions to Form 706, p. 4.

IRC Chapter 13 imposes a GST tax on all transfers, whether made directly or indirectly, to “skip” persons. Under IRC §2613(a), a skip person includes a person who is two or more generations below the generation of the transferor or a trust, if all of the interests are held by skip persons. Under IRC §2611(a), transfers subject to the GST tax are direct skips, taxable distributions, and taxable terminations.

IRC §2602 provides that the amount of the GST tax imposed on a transfer is determined by multiplying the amount transferred by the “applicable rate.” Under IRC §2641, the applicable rate is the maximum federal estate tax rate multiplied by the “inclusion ratio.” The inclusion ration is one minus the “applicable fraction.” The applicable fraction is a formula designed to reflect the property that will be taxed under the GST tax rules. The GST tax exemption is the numerator of the fraction. Therefore, if more of the GST tax exemption is allocated to the transfer, the fraction will be greater, the inclusion ratio will be less, and the GST tax with respect to the transfer will be less.

IRC §2631 allows every transferor a GST exemption that may be allocated to transfers made by the transferor either during the transferor’s life or at death. Affirmative allocations of GST exemption are generally made on Form 709. Under IRC §2642(b)(1), if a transferor allocates GST exemption on a timely filed gift tax return, the transferor may allocate an amount of the GST exemption equal to the value of the property on the date of the transfer to reduce the inclusion ratio to zero.

Automatic allocations of GST exemption are made under IRC §2632 to certain transfers made during life that are direct skips, so that the inclusion ratio for such transfers may be reduced to zero even without any affirmative allocation of GST exemption.

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I.R.S. Says Its Audits of Wealthy Are Rising

The Internal Revenue Service is intensifying its scrutiny of wealthy Americans.

The federal agency increased its audits of taxpayers who earned $1 million to $5 million by 33 percent last year compared with 2008, new I.R.S. figures show.

The numbers, released late Thursday in the agency’s 2009 annual data book, also show that the I.R.S. increased its audits by 16 percent for those earning $5 million to $10 million last year. Audits of those who made at least $10 million rose by 8.5 percent, according to the data.

The figures are the strongest evidence yet that the agency is honoring a vow by the I.R.S. commissioner, Douglas H. Shulman, to increase scrutiny of wealthy taxpayers.

Taxpayers who earned at least $1 million a year made up 0.25 percent of the more than 144 million individual federal returns filed last year, the data showed, but affluent Americans account for a far greater share of the underpayments in federal income tax returns.

“The 2009 results show our emphasis on higher-income individuals,” Bruce I. Friedland, an I.R.S. spokesman, said Friday in a statement. “We will continue to focus our enforcement efforts on high-income taxpayers, particularly those hiding their assets overseas.”

Tax specialists said Friday that the new data showed a surprisingly strong increase in the agency’s scrutiny of the affluent. “There is definitely a new focus on what we call high-dollar audits,” said Richard Boggs, the chief executive of Nationwide Tax Relief, a company in Los Angeles that helps taxpayers negotiate settlements of tax bills with the I.R.S.

“The I.R.S. is getting smart,” he said. “They are starting to better leverage their time, resources and talent in order to collect the most money. There is a definite shifting of the tide.” He said audits of those making at least $10 million rose slightly less than for other categories because so many of the ultrawealthy were already being audited.

Mr. Boggs said the 2009 I.R.S. data showed that taxpayers who made at least $1 million had an 8 percent chance of being audited last year, meaning about one out of every 12 was scrutinized — up from 6 percent in 2008, or nearly one in 17.

The I.R.S. created the Global High Wealth Industry Group last fall to scrutinize people earning at least $10 million a year. It focuses on deciphering the techniques the wealthy sometimes use to illegally minimize their tax bills. Those techniques include the use of partnerships, trusts and offshore entities.

The I.R.S. is also sorting through more than 15,000 disclosures filed by wealthy taxpayers last fall as part of an amnesty program aimed at luring out of hiding taxpayers who had not reported income hidden overseas.

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Refinancings Before and After § 1031 Exchanges

Cash (“boot”) received in a like-kind exchange results in taxable gain to the extent of realized gain. If the taxpayer exchanges Greenacre, whose adjusted basis is $1 million, for $1 million in cash and Whiteacre, worth $1 million, the taxpayer will pay capital gains tax on the entire $1 million cash received, since boot received equals realized gain.

Can the taxpayer can avoid the taxable gain in this situation by borrowing $1 million against Greenacre prior to the exchange? In that case, the fair market value of Greenacre, net of mortgage, would be only $1 million. In exchange for Greenacre, the taxpayer would receive Whiteacre, but not the $1 million in cash. Apparently, there would be no taxable gain, since the taxpayer received no boot in the exchange. Economically, two scenarios are nearly indistinguishable. In both cases, after the dust settles, the taxpayer will have $1 million in cash and a $1 million mortgage.

The Regs contain no prohibition on pre-exchange financing. However, the IRS may challenge such financing unless the debt is “old and cold.” Thus, while Regs. § 1.1031(b)-1(c)  treats a new loan obtained shortly before an exchange of relinquished property secured by that property as bona fide debt, the IRS may view that loan as cash received on the disposition of the relinquished property unless the loan has “independent economic significance.” A loan obtained to “even-up” the mortgages prior to the exchange solely to prevent gain recognition to one of the parties to the like-kind exchange would not appear to have independent economic significance.

To avoid IRS recharacterization, the refinancing (i) should be done by the exchanging party based on his own credit; (ii) should be possessed of a bona fide business purpose; (iii) should be made sufficiently in advance (i.e., “old and cold”) of any contemplated exchange to assure that the taxpayer is actually at risk; and (iv) the loan process should be commenced before the exchange is contemplated.

In contrast to pre-exchange financing, post-exchange financing poses less risk, since the taxpayer remains liable on the debt. No judicial or legislative authority appears to preclude a taxpayer from encumbering replacement property after the exchange. Still, to avoid the step-transaction doctrine, post-closing financing should be separated from acquisition financing. When closing title, excess financing proceeds should not be taken out at closing of the replacement property. Any refinancing should be done later and off the replacement property closing statement.

Adverse tax consequences can however flow from post-exchange refinancings if proper planning is not done to preserve the interest deduction on refinancing indebtedness. Since rules governing deductibility of interest depend on the type of interest involved, the proper classification of interst expense is essential to determine its deductibility. In general, interest expense on a debt is allocated in the same manner as the dcbt disbursed. Property used to secure the debt is immaterial. Temp. Reg. § 1.163-8T(a)(3).

Thus, investment of proceeds in tax-exempt bonds will result in a denial of the interest deduction on a mortgage against the replacement property. Likewise, use of refinancing proceeds for personal purposes will result in denial of the interest deduction. The deduction for “investment interest” is limited to “net investment income.” Investment interest is interest allocable to property held for investment, but not interest taken into account under the passive activity loss rules, or active business income. Therefore, even investments in taxable securities may result in denial of the interest deduction to the extent the interest expense exceeds the taxpayer’s investment income from such securities. Interest from active business income is subject to no limitations on deductibility.

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