Guest Article Archives - Page 11 of 52 - Think Outside the Tax Box
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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OBBBA Rundown: Provisions Affecting Businesses for 2025

Enacted into law on July 4, 2025, the One Big Beautiful Bill Act is the biggest set of tax law changes since the 2017 Tax Cuts and Jobs Act (TCJA). The provisions discussed in this article impact business taxpayers for tax year 2025 and must be considered immediately for proactive tax planning purposes, future tax withholding, and estimated tax payment calculations. Clients have questions, and we can generally give them the answers they seek; however, some will require future IRS guidance for complete clarity.

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Big, Beautiful, and Oh So Salty: SALT and the OBBBA

The SALT cap has been one of the most argued pieces of the One Big Beautiful Bill Act as it has been making its way toward passage. Actually, tax professionals and politicians have been talking about the SALT cap (and looking for ways around it) since it was enacted as part of the Tax Cuts and Jobs Act. As most of you are aware, most TCJA provisions were set to expire at the end of 2025, including the SALT cap. We take a look at where they stand now.

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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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Observations on the House-Passed OBBB

This article focuses on the OBBB from the House offering a variety of observations to help understand the range of changes, relevance to compliance and planning, process considerations and some unexpected provisions. While the final OBBB will not include all of the House provisions or will modify some of them, there are lessons to learn to understand the tax legislation process and results now and in the future.

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Client Retention as a Prospecting Strategy: Turning Current Clients into Referral Sources

In the competitive accounting world, where trust and reliability are paramount, client retention is not just a success metric—it's a vital strategy for sustainable growth. For Certified Public Accountants (CPAs), accountants, and bookkeepers, maintaining a solid relationship with existing clients can unlock new business opportunities, turning satisfied clients into powerful referral sources.

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Helping Elderly Clients Avoid Tax Scams

Taxes are scary enough, even without the threat of scammers involved. While technology has in some ways made taxes easier than ever, like any tool ever invented by humans, these new technologies have also become the plaything of scammers looking to pull off cons. Elderly clients who often have large life savings can be easy targets for scams, whether because of social isolation or emotional and cognitive problems, or maybe just because they didn’t keep up with the latest IRS or FBI warnings about being careful on the internet. Some elderly victims learn too late that it takes serious effort to resolve thefts of money – and potentially years to fix identity theft. These clients need to be extra vigilant. Here’s what to tell them.

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Client Alert

Beyond Numbers: How Post-Cognitive Accountants Transform the 1040 into a Portal of Profound Insights

In an era where Artificial Intelligence (AI) effortlessly handles the computational heavy lifting of tax preparation, the role of the accountant is evolving into something far more profound. The Post-Cognitive Accountant emerges not as a number cruncher but as a holistic advisor, transforming mundane tax documents into gateways of deep personal and financial insight. The once straightforward Form 1040 is now a rich tapestry, each box a doorway into the unique narrative of an individual's life. Let's embark on a journey through the 1040, reimagined as a portal to new dimensions of understanding and opportunity.

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