Guest Article Archives - Page 23 of 51 - Think Outside the Tax Box

Guest Article

By Randy Sadler, CIC Services

Perspectives on IRS Scrutiny of Captive Insurance Elections

The Internal Revenue Service has made no secret of its increased scrutiny of captive insurance arrangements, particularly those involving the small insurance company election. For taxpayers and their advisors, this has created understandable concern and, in some cases, hesitation about whether captive insurance remains a viable risk management and tax planning tool. Yet heightened scrutiny does not mean prohibition. The Internal Revenue Code continues to recognize captive insurance, Congress has refined it, and courts evaluate it based on well-established insurance principles. The real issue is not whether captives are allowed, but whether a specific taxpayer has a legitimate business need for insurance, has structured the arrangement properly, and has implemented it in a manner consistent with both tax law and insurance fundamentals. Understanding where scrutiny arises, how elections function, and what separates compliant captives from problematic ones is critical for CPAs advising closely held businesses today.

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How to Differentiate Yourself as an Accountant

In a highly competitive business landscape, even we accountants face the challenge of setting ourselves apart from our peers. The accounting profession has changed significantly in recent years, with technological advancements, changing regulations, and shifting client expectations. To thrive in this environment, as accountants, we must possess strong technical skills and differentiate ourselves by offering unique value to our clients. The hardest part of establishing our unique value is objectively looking at our accounting journey and pinpointing our most significant achievements.

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A ChatGPT Plus User’s Guide to Effortlessly Creating Custom GPT Apps with GPT Builder

In an astonishing breakthrough that’s flipping the tax world on its head, certified tax planners now have the power to craft their very own AI-powered tax genie, thanks to the revolutionary GPT Builder. Gone are the days of sifting through stacks of tax codes and legislation. With a few clicks and a sprinkle of AI magic, these financial wizards are conjuring up custom tax strategies that promise to save fortunes. Dive into the future of tax planning where technology meets savvy to create the ultimate tax-saving ally. This isn’t just a game changer; it’s a wealth transformation phenomenon!

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An S Corporation Basis Decision That You Need to Know About

The Estate of Thomas H. Fry v. Commissioner is an opinion that anybody who deals with S corporations needs to know about. You may have read about it as a taxpayer win and it is. Another reading is that it is a cautionary tale to not do what Thomas H. Fry and his team did with his S corporations, Crown Disposal Inc (CD) and CR Maintenance Services Inc (CRM). Think of the win part of this opinion as a life jacket that might come in handy if you run your ship into the rocks. Better you should pay attention to the rocks and avoid them.

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Revolutionizing Client Engagement: The Shift from EPTI to PAVER in Tax Reporting with Generative AI

Are you seeking innovative strategies to elevate your client reporting processes? Wondering how to transition from traditional methods to more engaging and personalized interactions? The emergence of generative AI has instigated a profound transformation in the domain of client communication for tax planners, shifting from the conventional Email, PDF, Telephone, In-person (EPTI) reporting techniques to a more advanced PAVER framework. Read on to find out more!

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Hobby Loss Developments in 2023

The laws of tax planning that I developed over my writing career that will be expounded in the upcoming Reilly’s Laws of Tax Planning, published by Think Outside the Tax Box, lean a little on the conservative side, as tax planners use the term – conservative versus aggressive, not conservative versus liberal. This results, in large part, from their primary source being court decisions. The 18th law stands out from the others in this regard. “Honest objective trumps realistic expectation” encourages practitioners to be somewhat more aggressive in claiming losses from activities that seem a little dubious . I still hold that view, even though there have been no encouraging developments in 2023. Here is a roundup on the action last year through December 2, 2023.

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Crypto Gains and Tax Court Games: Exploring the “Unclean Hands” Defense

Baseball, apple pie, and finding creative ways to pay fewer taxes, is there anything more American? Judge Learned Hand famously said in 1934, “Any one may so arrange his affairs that his taxes shall be as low as possible; he is not bound to choose that pattern which will best pay the Treasury; there is not even a patriotic duty to increase one’s taxes.” Since the inception of the Federal Income Tax, taxpayers have looked for increasingly creative ways to avoid it. This exploration is no different: A taxpayer attempts to wash his hands of his tax liability all together.

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TAX COURT ROUNDUP – MARCH 2024

February was Discovery Month at Tax Court. The high-deficiency, high-profile conservation easement cases coming from IRS crackdown put a premium on the old continuing legal education staple "win your case at discovery." But it doesn't go so well for shotgun demands, nor for broad-spectrum claims of privilege. Of course, more was resolved than just discovery disputes, but I'll get to those.

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Soapbox Ethics: Circular 230 And the Unauthorized Practice of Law

The beneficial ownership reporting requirement established by the Corporate Transparency Act has created a fair amount of chaos concerning whether providing reporting services to clients is the unauthorized practice of law (UPL). While some state bar associations have come down on one side or the other as to whether certain types of reporting are UPL, the Treasury offers no clear guidance. What the IRS has made clear recently is that Circular 230 ethical obligations extend to matters beyond what the Loving case determined was “practice before the IRS.”

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