Is that Side Hustle a Business or Hobby?

Income Tax, Tax, Tax Controversy, Uncategorized

Hobby loss tax rules of IRC § 183 are nothing new. However, there are a couple of recent developments that make the application of those rules especially relevant: Starting in 2018, the Tax Cuts and Jobs Act (“TCJA”) went into effect. Under the TCJA, taxpayers lost the ability to take miscellaneous itemized deductions. Previously, taxpayers…
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Transfer to Third Party at Direction of Beneficiary Deemed Gift from Beneficiary

Estate and Gift Tax, Estate Planning, Tax, Tax Controversy

In a newly released Chief Counsel Advice opinion[1], the transfer of assets from a foreign entity referred to as the “Foundation” directly to a third party (the “Recipient”) at the request of the beneficiary of the Foundation (the “Beneficiary”) was deemed to be a gift from the Beneficiary to the Recipient. This is a logical…
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Ninth Circuit says Nice Try on Passive Rental Activities

Income Tax, Tax, Tax Controversy

Introduction The U.S. Court of Appeals for the Ninth Circuit recently affirmed a District Court’s ruling against a married couple who claimed their losses related to three vacation properties were not limited under the passive activity loss rules of IRC § 469.[1] The couple argued that the management company responsible for renting the property to…
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Lothringer and Alter Ego

Business Transactions, Income Tax, Tax, Tax Controversy

A recent case shows how a shareholder and corporation, being considered alter egos, can cause unintended consequences. In Lothringer,[1]a corporate shareholder’s individual property was subject to enforced collection action by the IRS to satisfy corporate tax liabilities.[2] The court’s finding that the corporation was the shareholder’s alter ego allowed the IRS to hold the shareholder…
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Gifting Appreciated Stock Before Redemption – Dickinson

Business Transactions, Charitable Giving, Estate Planning, Tax, Tax Controversy

Introduction Generally, a taxpayer may deduct the fair market value of appreciated property donated to a qualified charitable organization.[1] This provision expands the benefits available to taxpayers with respect to charitable deductions. The result, in effect, is that a taxpayer may gift an appreciated asset in lieu of selling the asset, paying tax, and then…
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Non-profit Corporation Denied S Corporation Election

Income Tax, Tax, Tax Controversy

In a recent Tax Court opinion, the Court granted the IRS’ motion for summary judgment holding that a state law Nonprofit corporation could not election to be treated as S corporation for federal income tax purposes.[1] Clinton Deckard attempted to make an S election for Waterfront Fashion Week, Inc., a Nonprofit corporation organized under the…
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