Feature Article Archives - Think Outside the Tax Box
By Keith Schroeder, EA

Tackling Taxes On an Inherited HSA

The Health Savings Account (HSA) is a first line of defense tax strategy. Contributions are deductible and earnings are tax-free if used for qualified medical expenses. There are numerous features to the HSA that secure maximum tax benefits. Structured properly, an HSA can provide serious tax-free money to beneficiaries as well as the account holder. Before we review the implications of inheriting an HSA, let’s review some of the powerful features an HSA has that increases the value of the account.

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Tax Tales I Let Slip in 2025: From Whistleblowers to Easement Woes and Beyond

One of my greatest frustrations as a tax writer is that I just don’t have the time to cover everything that I notice. Early in my blogging career, when I was younger and had more energy, I set myself on a Monday, Wednesday, Friday schedule like the college professors I envied. Even that did not keep up with everything I noticed, so periodically I would do a post that had short blurbs about interesting things I didn’t dig further on. Here is an example from 2010 of a post that covers an entity not considered a church by the IRS, S corp shareholder basis issues, definition of alimony and two Chief Counsel Advices on TEFRA issues. So here are some things for 2025, that I opened a file on but never managed to make an article with.

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This Is The Only Other Year-End Tax Tip Guide You Need

So as I did last year, I have reviewed a multitude of year-end tax tips articles. One of them is a real standout that you should be sure to check out. If you missed it, you should definitely roll back to the November 15 edition and go over Dominique Molina’s piece, which focuses on what you need to do sooner rather than later in response to OBBBA. It provides more detailed, relevant, actionable advice that you won’t see anywhere else than any of the multitude of pieces I have reviewed. As for the rest, I will give you a basic rundown of what I call the SOSO (same old, same old) and a few suggestions that stand out as different that I will get into a little more along with some thoughts of my own.

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Lessons Learned from the Tax Court: The Root of the Issue

When is a business really a business? As Supreme Court Justice Potter Stewart said in 1964, “I know it when I see it.” The US Tax Court, however, maintains a slightly less subjective standard. The Roots were pretty sure they were running a bona fide business; the IRS, however, didn’t share the sentiment. And since we’re reading about them in a segment called “Lessons Learned,” one should assume it did not go the way the Roots would have liked.

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Year-End Tax Planning Under the One Big Beautiful Bill Act (OBBBA)

The One Big Beautiful Bill Act (OBBBA), signed into law on July 4, 2025, doesn’t reinvent the tax code it refines it. Much like its predecessor, the Tax Cuts and Jobs Act (TCJA), it keeps many familiar provisions in play: lower rates, expanded SALT flexibility, and broader deductions. But here’s the real story: While most tax pros are busy memorizing what stayed the same, the planners who will win 2025 are the ones spotting what just became possible. OBBBA quietly opens a handful of powerful new planning windows — each one capable of delivering real, measurable savings for the right client. The key is knowing which changes are worth your time… and which are just political garnish. Below, we’ve curated the most strategic, high-impact moves to make before year-end 2025, the ones that separate the advisors who explain the law from those who leverage it. Most tax pros will stop at what changed. The smart ones will keep reading to learn how to use it.

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Client Alert

An Analysis of the OBBBA’s Trump Accounts (Part 2)

In part one of this series, I went over the basics of the new retirement accounts for minors, Trump Accounts, which were created as part of the One Big Beautiful Bill Act (OBBBA). Trump Accounts allow the Government, Charitable Organizations, Parents, and others to contribute to a child’s savings, usually on an after-tax basis. These accounts then transition to a traditional individual retirement account (IRA) when the child turns 18. Although the contribution limits act like non-deductible traditional IRA contributions and have a contribution limit of only $5,000 per year, they do not have the same earned income requirements that traditional IRA contributions have. This means that children are able to accumulate savings even without earned income. This article presents several scenarios to examine how Trump Accounts may play into an overall savings strategy for children.

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An Analysis of the OBBBA’s Trump Accounts (Part 1)

The One Big Beautiful Bill Act, signed into law by President Trump on July 4, 2025, added a new tax saving tool for minors, the aptly named Trump Accounts. In this article, I go over the details of the new Trump Accounts. In part II, I will discuss some of the potential tax planning opportunities and pitfalls related to the new accounts.

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Client Alert

Is It Time to Hire in Your Firm?

After my second busy season as a solo practitioner, I made a terrible mistake within my firm. I hired my first employee. As a matter of fact, I hired someone who also had tax and accounting experience. You may be thinking, “What? Hiring is the solution if you were feeling overwhelmed.” That is true, if you are assuming that I had the proper systems in place. The mistake I made was hiring an employee before I was ready. The money was there and ready. The work was there and ready. It only took a few weeks to realize that I didn’t have a capacity issue. I had a systems and processes issue. I am not suggesting that you should work yourself to full capacity, absolutely not. I am suggesting that before you attempt to pass along a task to someone else or put in place automation that you have a written-out process.

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Qualified Opportunity Zones After the One Big Beautiful Bill Act: What’s Changed and What It Means for Real Estate Investors

On July 4, 2025, the One Big Beautiful Bill Act (OBBBA) became law, representing the most significant reform of the QOZ program since its inception. It made the program permanent, tightened eligibility rules, introduced a rural-focused investment vehicle, and imposed robust reporting requirements. For tax professionals and investors, understanding these changes isn’t just about compliance – it’s also about strategy.

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Client Alert
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