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Loopholes

By Peter J Reilly CPA

Syndicated Easements: Fresh IRS Offer and the Perils of Post-BBA Gamesmanship

The IRS has issued a statement about a new settlement offer that is going out for conservation and historic preservation easement disputes. It is similar to previous offers, but there is one big difference. The partnership will not have to make a payment at the time that it accepts the offer. Other than that, it is similar to the deal offered in 2020. Taxpayers get to deduct what they are out-of-pocket as an ordinary deduction and are subject to a 10% penalty. In general, the out-of-pocket donation might be around 20% to 25% of the claimed charitable deduction. The Tax Court, on average, has been allowing 6%, although results vary. There is usually a 40% penalty in the decided cases.

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The Corporate Vault: How to Use a C Corporation to Stockpile Cash for the Future

When most people think about saving for the future, their minds jump to retirement accounts—401(k)s, IRAs, maybe even defined benefit plans. But business owners have another option that often goes overlooked: using a C corporation as a strategic savings vehicle. By leveraging the flat 21% corporate tax rate, smart income shifting, and careful timing of distributions, business owners can “stockpile” cash inside a corporation, building wealth for future use without the red tape of traditional retirement plans. Want to see how top tax strategists legally use C corporations as private retirement vaults while avoiding double taxation and IRS scrutiny? Continue reading to learn the blueprint.

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TAX COURT ROUNDUP – December 2025

An updated website launches, the economic substance codification is applied, Loper Bright Entrprs. marches on but hits the statute, and the syndicated conservation easement flood continues, as Tax Court pushes through the government shutdown. The biennial examination for non-attorney admission to Tax Court took place as scheduled.

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TAX COURT ROUNDUP – November 2025

Though the government was shut down all month, and trial sessions were canceled, Tax Court carried on. Online improvements were forecast, the equitable tolling saga continued, and self-represented novelties featured this month.

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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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