Estate Planning in Volatile Markets

Anyone paying attention knows that stock markets have been volatile. As a simple example, the Dow Jones Industrial Average saw an increase of over 600 points (1.56%) on April 11 after dropping over 1,000 points (2.5%) on April 10. Similarly, the S&P 500 gained 9.5% on April 9, but dropped 3.5% on April 10. Generally,…
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Recent Microcaptive Case Undermines Promoted Structure

A recent Tax Court decision underscores an increasingly rigorous examination of Section 831(b) microcaptive insurance arrangements.[1] This ruling may be insightful to taxpayers considering or currently operating microcaptives, has broad implications for businesses seeking legitimate tax incentives created by Congress. Overview of the Case The case at hand involves the Internal Revenue Service’s (“IRS”) rejection…
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With Tax Season Upon Us, Only Take Deductions That Can Be Substantiated

With the filing deadline for individuals to file their income tax returns approaching and people becoming more acutely aware of how much in taxes they will pay for the last year, now, perhaps more than other times of the year, I receive comments from people about “starting an LLC to reduce taxes,” or “having expenses…
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Death of Grantor: Conversion of LLC to Tax Partnership

Common in estate and trust planning is the gift or sale of assets to an irrevocable grantor trust[1] structured to be outside of the grantor’s taxable estate.[2] Often, such gifts or sales are made of interests in family entities such as LLC’s.[3] These entities can provide significant non-tax benefits including consolidation of assets, centralized management,…
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Weston v. Comm’r: A Cautionary Tale on Loss Deductions and Tax Compliance

In a recent Tax Court decision, the Court again approached the critical issues surrounding loss deductions and tax compliance.[1] This case involves Heather and Stewart Weston, a married couple from California, who claimed a $2.1 million loss deduction on their 2017 tax return tied to failed business ventures in Indiana. The Internal Revenue Service (“IRS”)…
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Substantiate Those Deductions, But Not with Falsified Documents!

We have written numerous articles over the years about substantiating deductions, whether they be charitable donations or business expenses or any other type of deduction.[1] As noted by the Supreme Court, deductions “are a matter of legislative grace, and taxpayers bear the burden of proving their entitlement to any deduction claimed.”[2] A recent Tax Court…
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CCA 202504016 and Amended Returns

Most U.S. citizens are familiar with the concept of filing an income tax return. As with any other work product, errors and omissions can occur in tax returns. Once a tax return has been filed, the taxpayer can generally only correct the return by filing an amended tax return. The IRS recently published a third-party…
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Closely-Held Family Partnerships: New Reporting Obligations

Treasury recently finalized regulations imposing significant reporting obligations on persons involved in what the regulations describe as “related party basis adjustment transactions.” These regulations designate such transactions as “transactions of interest,” a form of reportable transactions.[1] Reporting obligations can apply to transactions completed prior to the date of these regulations and also may extend many,…
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