Guest Article Archives - Page 5 of 52 - Think Outside the Tax Box

Guest Article

By Peter J Reilly CPA

What’s New With Hobby Loss: Recent Developments in Section 183

Recent developments in the Section 183 (Hobby loss) area have not led me to change my basic conclusions. Taxpayers who have a sincere objective of ultimately making a profit should not hesitate to claim losses from the underlying activities. That is so even if you believe that profits are improbable. It is critical that they meet the standard of behaving in a businesslike manner. The other regulatory factors should not be ignored, but often there is not that much you can do about them. Reilly’s 18th Law of Tax Planning – Honest objective trumps realistic expectation.

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Help Clients Rebuild Tax Records After Disaster

Tax pros help clients with a lot of catastrophes: wrangles with tax authorities, paltry nest eggs, more wrangles with tax authorities. More frequently, your clients might face a more tangible and cinematic disaster. These days, there’s always a storm comin’. Swept away in that destruction, for many people, are physical tax and financial records. A few precautions could have prevented such loss and made life at least a bit easier for victims. Here’s how to help clients head off trouble – and recover after it hits.

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Client Alert

George M. Cohan’s Tax Triumph: The Rise and Erosion of the Cohan Rule

The Cohan rule is named for George M. Cohan. George Michael Cohan (1878 – 1942) was a theatrical producer. In the decade before World War I, he was called the “man who owned Broadway” and is considered the father of American musical comedy. In 1940 he was awarded the Congressional Gold Medal for his contribution to morale during World War I with his songs “You’re a Grand Old Flag” and “Over There,” the first time the medal was awarded to someone in an artistic field. But his most enduring legacy may be the tax rule that shared its name.

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AI Risk Management Frameworks for Tax Accountants

Let’s be direct: AI is one of the most powerful capacity tools tax professionals have seen in decades. Used correctly, it buys you time you can reinvest into high-value advisory: planning, structuring, audits, negotiations, strategy, client education, and relationship building. But here’s the catch that you as an elite tax practitioner already understand: aggressive planning requires rigorous defensibility. If you’re going to use AI to accelerate complex planning work, your defense file must be stronger, not weaker. This playbook gives you that: a practical framework that keeps you safe while you scale.

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Start the Year Right: Your WISP Doesn’t Have to Be a Tax Season Nightmare

The mere mention of a WISP makes most tax professionals want to suddenly lose their internet connection. It sounds bureaucratic, technical, and deeply unfun. But here’s the good news: creating and maintaining a WISP does not have to feel like a compliance root canal. And ignoring it can turn into something far worse than an IRS audit. Let’s talk about why you need one, what it’s actually supposed to do, and how to get it done without wrecking your sanity in the middle of filing season.

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Fleeing High Tax States And The Stickiness Of Domicile

Part of preparing to leave a high state tax is facing up to the fact that the tax collectors of high-tax states can be kind of clingy. There is more to changing your residence for tax purposes than simple steps like a new driver’s license and a change in voter registration.

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Stop Selling Hours – Start Selling Impact

For decades, accountants have been taught one core billing truth: Time equals value. You bill time, track time, manage time, and measure profitability by time. As a staff auditor, I recall conversations about "stay within the billable hours," but I always found it conflicting. If the scope grew, why wouldn't we charge for the additional time required? Over the past five years, I have seen this topic come up at summits and conferences. I even did a few presentations as I learned how to charge differently. Now, more firms are realizing that time-based pricing is killing their growth, profitability, and positioning. Time-based pricing cheapens your expertise, anchors your value to effort instead of outcomes, and commoditizes your knowledge. It is time for accountants to stop selling hours and start selling impact.

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TAX COURT ROUNDUP – February 2026

I can’t say that 2025 was anything less than tumultuous, or that 2026 isn't likely to be more of the same. Boechler, P. C., Jarkesy, Zuch, the Affordable Care Act, FBAR, and even long-gone FASIT and SDLIA are already starting the year. Come along for the ride!

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Kadau v. Commissioner and the Line Between Effective and Broken Captives

Captive insurance remains one of the most closely examined tax planning strategies in use today, not because it is inherently flawed, but because small missteps can carry outsized consequences. Many taxpayers assume that careful formation and proper documentation are enough to protect the intended tax outcome. A recent Tax Court decision, Kadau v. Commissioner, serves as a reminder that those assumptions deserve closer scrutiny. The court’s analysis did not hinge on whether captive insurance can work, but on how a specific arrangement actually functioned in practice. For tax professionals advising clients who rely on micro-captives, the case raises important questions about where structures tend to break down, why some arrangements attract IRS attention while others do not, and what really separates a defensible captive from one that invites challenge.

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