Loopholes Archives - Think Outside the Tax Box
By Lewis C. Taishoff

TAX COURT ROUNDUP – November 2025

There are new insights and old unresolved questions in this month's instalment. There's always the old and new.

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Taxes & Taxidermy: Rampaging Through The Tax Code On The Back Of A Stuffed Rhinoceros

Is the taxidermy fee for a stuffed bear deductible? If so, should I depreciate it? What would the basis and class life be for depreciation? Those are real questions asked in a group chat with some colleagues. Of course my answer was “It depends.” And, like all good tax professionals, I proceeded to ask a series of follow-up questions. And, like a good writer, that got me to thinking about all of the tax-related case law surrounding taxidermy and what it can teach us—it’s more than one might think.

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TAX COURT ROUNDUP – October 2025

There are new insights and old unresolved questions in this month's instalment. There's always the old and new.

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2025 Winter Education Series Event Calendar

Think Outside the Tax Box proudly presents the 2025 Winter Education Series! This October through December, we are bringing our loyal subscribers five webinars featuring some of the brightest minds in tax. Each high quality webinar is filled with engaging content, actionable insights for your clients, and they all come with continuing education credits for those who qualify. All of this is included in your regular subscription! Check out what we've got in store for you!

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TAX COURT ROUNDUP – September 2025

If reviewing Tax Court opinions teaches one thing, it's that tax legislation is too important to leave to legislators. Tax Court Judges are hyper-qualified; they need to be, to deal with what this month shows.

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TAX COURT ROUNDUP – August 2025

This month's Tax Court cases feature warnings to lawyers (and appraisers?) in the ongoing syndicated conservation easement wars; teasers about the impact of Loper Bright Ent. and Section 7701(o)(1); useful practice tips, and the conclusion of Boechler, P.C. (equitable tolling won't save a losing case).

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The Think Outside the Tax Box OBBBA Quick Reference Guide

The One Big Beautiful Bill Act (OBBBA) marks the most sweeping overhaul of the tax code since 2017, reshaping rules across personal and business income, education, healthcare, and credits. To help you stay ahead of the curve, Think Outside the Tax Box is proud to share our Quick Reference Guide, designed to keep you and your clients informed, prepared, and proactive.

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Campaign Promises and the OBBBA: Always Read the Fine Print

The One Big Beautiful Bill Act makes good on several promises President Trump made on the campaign trail. Of course, tax legislation, unlike campaign sloganeering, rarely lends itself to sound bites. It is the opposite of pithy and the opposite of memorable. Even the bill’s title pushes the boundaries of memorability. If you’re looking for the tax promises section of the OBBBA it is in Title VII–Finance, Subtitle A–Tax, Chapter 2–Delivering on Presidential Priorities To Provide New Middle-Class Tax Relief. We take a closer look in this article.

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TAX COURT ROUNDUP – July 2025

Something old, something new, is the usual product of Tax Court, and this month is no exception. New: Equitable tolling is applied to out-of-country petitioners (maybe), an abandoned corporate merger escapes Section 1234A capital loss treatment of a break-up fee, the discounted cash flow method of valuation is rejected for valuing conservation easements, and the S.E.C. v. Jarkesy Eighth Amendment controversy continues. Old: Erroneously addressed Notices of Deficiency, witness testifying remotely, sealing witness testimony, CDP is a snapshot, and debt-vs-equity.

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