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Avoiding Passive Loss Limitations Through Short-term and Alternative Rentals
Short-term rentals like AirBnb are becoming increasingly popular with taxpayers who invest in real estate. For many taxpayers, the appeal of these properties is the flexibility and cash flow potential. However, there may be an overlooked third tax benefit. In many situations these short-term rentals may not qualify as a rental activity to the IRS, and that may offer a big tax break. While many rental activities generate losses, this can leave taxpayers facing the frustrations of not always getting to deduct those losses right away due to the passive activity limitations.
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What Happens If You Can’t Use All Your Clean Energy Tax Credits This Year?
Clean energy tax credits have a lot going for them. Clients buy them at a discount, apply them dollar-for-dollar against federal tax liability, and walk away paying less to the IRS. That alone makes them worth a serious look. But here’s what often gets overlooked and what makes these investments genuinely remarkable compared to almost anything else in your tax planning toolkit: the flexibility built into how and when the credits can be used. Can’t absorb the full credit this year? Carry it back up to three years and trigger refunds on taxes your client already paid. Think about that for a second. There are very few places in the tax code where you can go back in time and rewrite last year’s tax bill. This is one of them. Still have excess after the carryback? Carry it forward for up to 22 years. That’s not a typo. Two decades of runway to put those credits to work as your client’s passive income grows. And if circumstances change and the credits simply aren’t needed? An emerging secondary market means there may even be an option to sell them. No other common tax planning strategy offers this combination a guaranteed discount on purchase, dollar-for-dollar offset of tax liability, the ability to look backward and forward, and a potential exit if plans change. Understanding how each of these features works is what separates a good credit investment from a great one.

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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2025 Winter Education Series Event Calendar
Think Outside the Tax Box proudly presents the 2025 Winter Education Series! This October through December, we are bringing our loyal subscribers five webinars featuring some of the brightest minds in tax. Each high quality webinar is filled with engaging content, actionable insights for your clients, and they all come

Charitable Impacts of the One Big Beautiful Bill Act
For charitable-minded taxpayers, several provisions in the One Big Beautiful Bill Act (OB3 Act) will impact the tax reduction associated with their charitable giving starting next year in 2026. In one case, the change increases the deductible amount, but all other changes surprisingly reduce the value of charitable contribution deductions.

The End of the Green Road? The One Big Beautiful Bill and Energy Credits
Just when many believed green tax incentives were firmly established, the One Big Beautiful Bill (OB3), formally designated as Public Law 119-21 and enacted on July 4, 2025, delivers a sudden and sweeping rollback of key energy tax credits. Affecting everything from electric vehicles to rooftop solar, OB3 significantly alters

Editor’s Pick: Tax Planner Faces Malpractice Claims Over Decades-Old Tax Advice—What Went Wrong?
In a case that every tax professional should take note of, the prominent law firm Sidley Austin LLP finds itself defending against claims that it provided faulty tax advice over two decades ago, leading to massive IRS liabilities for a family. The plaintiffs, the Cáceres family, are seeking to recover
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Featured Authors
Amber Gray-Fenner is an Enrolled Agent and tax practitioner specializing in tax returns, planning, and representation for individuals and small businesses. She owns Tax Therapy, LLC in Albuquerque, New Mexico.
Matt Metras, EA, owns MDM Financial Services in NY, specializing in bookkeeping and taxation for cryptocurrency clients. He’s an educator on cryptocurrency taxation and actively engages in community advocacy.
Jeff Stimpson, has been a tax and finance writer for 25 years. Hee contributes to publications like Accounting Today and Financial Advisor. His other credits include sales tax, technology, and practice management, residing in New York.
Annette Nellen is a professor and tax program director at San José State University, with extensive involvement in tax organizations and a focus on tax policy, cryptocurrency, and education.
Peter J Reilly graduated from the College of the Holy Cross, worked in CPA firms like Joseph B Cohan and Associates and CCR LLP, and now runs a tax practice while writing for Forbes.com.
Thomas Gorczynski, EA USTCP CTP, is a tax expert known for speaking and educating on federal tax law. He’s editor-in-chief of EA Journal, co-author of the PassKey Learning Systems EA Review Series, and runs a tax practice in Phoenix, Arizona.
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