Income Tax Issues
Tax Articles

Reckless (albeit Tax Conscious) Abandonment under IRC § 165

Uncle Bill is somewhat of a hoarder.  In truth, the only thing that he has ever abandoned was his first wife…in a Waffle House at 2:15 AM on the outskirts of Norman, Oklahoma. In Bill’s defense, she had tried to stab him. In her defense, he probably deserved it. When Bill comes to you to chat about IRC § 165 losses—so-called “abandonment” losses—you know he has some hairbrained scheme in his head to stick it

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Scott St. Amand April 29, 2021
Income Tax Issues
Tax Articles

Successor Liability in a Purchase of Corporate Assets

As a tax controversy lawyer, most of your clients come to you in quite a predicament with the IRS, rather than coming to you to avoid said predicament. Such is the case when Cousin Elmer comes to visit you one dismal winter day. You may remember Elmer from our article on FBARs, but if not, Cousin Elmer has seven and a half fingers from trying, rather unsuccessfully, to eradicate his attic’s squirrel population through the

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Scott St. Amand April 29, 2021
Income Tax Issues
Tax Articles

The Cohan Rule and the IRC § 274 Exception

A taxpayer may deduct all ordinary and necessary expenses paid or incurred during the taxable year in carrying on a trade or business.[1] In contrast, a taxpayer may not deduct personal, living, or family expenses unless the Code expressly provides otherwise.[2] The determination of whether an expense satisfies the requirements of IRC § 162 is a question of fact for the Tax Court.[3] Proving Entitlement A taxpayer must prove his entitlement to all deductions and

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Scott St. Amand April 29, 2021
Income Tax Issues
Tax Articles

Personal Liability under the At Risk Rules

So, you have a business loss.  Join the club.  The real question is whether you have personal liability under the at risk rules of IRC § 465. Personal Liability under the At Risk Rules of IRC § 465 For certain taxpayers (including individuals and certain closely held corporations), who are engaged in certain activities (including each activity engaged in by the taxpayer in carrying on a trade or business or for the production of income),

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Scott St. Amand April 29, 2021
Income Tax Issues
Tax Articles

Examining the Method of Accounting and the IRS’s Broad Discretion to Change Them

The Practical Limits of IRC § 446(a) A taxpayer must compute taxable income under the method of accounting it regularly uses in keeping its books.[1] The IRS has rather broad statutory discretion to change a taxpayer’s accounting method in certain circumstances.[2] If the method of accounting used by the taxpayer does not clearly reflect income, the IRS generally will see fit to change the taxpayer’s method of accounting to a method that, in its not

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Scott St. Amand April 29, 2021
Income Tax Issues
Income Tax Issues

Deductibility of Fines and Penalties under New IRC § 162(f) Regulations

As you sat down one fine Tuesday morning in January 2021, and you cycled through the emails that rolled into your inbox in the 12 minutes since you last checked them, you notice an update announcing that the IRS is issued final regulations on IRC § 162(f) – deductibility of fines and penalties. You have had prior experience with the Code section, due to Uncle Bill’s penchant for minor violations of laws, regulations, and social

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Scott St. Amand February 1, 2021
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