Guest Article Archives - Page 2 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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The AI-Enhanced CPA: How to Automate Repetitive Work and Reclaim Advisory Time

There has never been a moment in the accounting profession, quite like this one. For decades, new tools have promised efficiency and accuracy, but artificial intelligence is different. AI is not just another tool, it’s a change in how we work. AI can automate tasks that were formerly part of our everyday work, such as data entry, reconciliations, reporting, and even initial research.

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Sirius Solutions and the S Corp or Partnership Choice

The Fifth Circuit Court of Appeals opinion in Sirius Solutions L.L.L.P. v. Commissioner may change our views of entity choice. If the decision holds up, partnerships will be able to effectively make the portion of limited partner income subject to self-employment tax whatever they want, including zero. This contrasts with the IRS position upheld by the Tax Court in Soroban Capital that treated all of the income of limited partners who were active in the business as self-employment income.

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Client Alert

Niche Down to Scale Up: How Specialization Drives Visibility and Profitability

For many accountants, narrowing our focus can feel risky. We are trained to serve anyone who needs help and provide stability in any financial situation. Choosing a niche often raises concerns: Will we turn away good clients? Will we limit opportunities or reduce business stability? These are common doubts many of us have faced in our careers.

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TAX COURT ROUNDUP – May 2026

April brings both anomalies and the same-old from Tax Court. Congressional enactments that misfire give opportunities to inventive practitioners, while self-represented petitioners continue to do the darndest things. All these are teaching moments that make "the small court" a continuing professional education course that never ends.

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The Kwong Tsunami: Why Form 843 Claims Could Soon Flood Your Practice

The buzz around the Kwong v. United States decision is quickly turning into something very real for practitioners: potentially a wave of Form 843 claims tied to COVID-era penalties and interest. With voices like Frank Agostino pushing for action, the message is clear: dig into client transcripts and don’t sit this one out, even though the outcome is still being litigated.

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The Strategic Tax Analysis Process: Your Systematic Approach

Early in my career as a tax professional, I thought identifying strategic opportunities was primarily a function of technical knowledge. If I just knew enough tax law, I assumed the right strategies would naturally reveal themselves when reviewing a client's situation. This assumption led to a haphazard approach where I might spot a planning opportunity for one client but completely miss an identical opportunity for another simply because I wasn't methodically looking for it. This inconsistent approach changed when, leaning on my training as an instrument rated pilot, it occurred to me that I should be following a structured process that assures that I won’t miss any opportunities. That observation transformed my practice. I realized that identifying strategic opportunities isn't just about what you know—it's about how systematically you apply that knowledge. Even the most knowledgeable tax professional will miss opportunities without a structured methodology for uncovering them. In this article, I'll share the systematic strategic analysis process I've developed over three decades of tax practice. This methodology doesn't replace technical knowledge—it magnifies its impact by ensuring you consistently identify opportunities across diverse client situations.

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The Brain Rust Effect: 100 Ways Accountants Are Fighting Cognitive Atrophy in the Age of AI

The accounting world is changing fast. Computers and AI now handle much of the boring, repetitive work that humans used to do by hand. This is great for saving time and catching mistakes, but it also introduces a new challenge: "mental rust" or “cognitive atrophy.” If we rely on computers for most of our thinking, our own problem‑solving skills can weaken. Recent studies suggest that heavy reliance on AI tools is associated with lower scores on some critical thinking tests. When we stop practicing how to solve problems ourselves, we may be less prepared when something unusual happens that the computer cannot handle. To stay sharp, accountants need to find practical ways to keep their brains working hard. Here are 100 simple ways to keep your mind strong in the age of AI.

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Untapped State Benefits for Veterans: Planning Opportunities for Advisors and Families

Two veteran clients with seemingly similar financial profiles can end up with very different outcomes, simply based on where they live and how informed they are. Much of that difference comes down to smaller, state-specific benefits that tend to sit just outside the typical planning checklist. But when layered alongside federal veteran benefits, they can reshape major decisions like where to buy a home or settle long-term. For advisors working with military families, recognizing how these state benefits show up in real life can go a long way in helping veteran clients feel seen, understood and better supported in the decisions ahead.

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