Free Article Archives - Think Outside the Tax Box
By Amber Gray-Fenner, EA NTPI Fellow USTCP

Fractional Art Investing Is Real — How To Advise Your Clients On The Tax Consequences

In mid-November a portrait of a young Vietnamese woman by the artist Gustav Klimt, which was part of the estate of the late Leonard Lauder (the cosmetics billionaire), was sold at a Sotheby’s auction for $236.4 million. It set the record for the most expensive work of modern art ever sold at auction according to Bloomberg. That’s probably out of reach for most of our clients. But what if they could join together to buy an interest in the painting with an entity holding the asset? That’s the idea behind the burgeoning fractional art market. While, in general, the art market has been struggling for a few years, the fractional art market has been expanding. According to the website Digital Original, “Fractional art ownership is no longer a niche concept – it’s a growing investment trend that’s accessible, flexible, and supported by cutting-edge technology.” What, you may be asking, does this have to do with taxes? It may be more than you think for your high-net-worth clients. As a trusted advisor it’s important that you are aware of both the types of investment opportunities your clients may be buying into and the tax consequences.

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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 with continuing education credits for those who qualify. All of this is included in your regular subscription! Check out what we've got in store for you!

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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. This article will review how the OB3 Act changed the charitable contribution deduction landscape and strategies for tax year 2025 and beyond to maximize the tax reduction value from charitable contributions.

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Client Alert

Some Tips to Help Clients Make the Most of the New Tip Tax Deduction

The One Big Beautiful Bill Act relieves some of the tax burden that comes along with tip income for tax years 2025-2028. But not in some of the ways that it was initially explained. Yes, tip income is still taxable income. No, customers do not have to pay tips in cash for them to be deductible. But the tip does have to be voluntary, qualified, and reported to the IRS.

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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 the tax landscape with abrupt cutoffs and a glaring absence of transition relief.

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Client Alert

2025 Summer Education Series Event Calendar

We are thrilled to bring you the 2025 Summer Education Series, sponsored by Vistia! All summer long we will be bringing our loyal subscribers monthly webinars featuring some of the brightest minds in tax. Each webinar will feature our usual blend of high-quality education and entertainment and include continuing education credits for those who qualify. All of this is included in your regular subscription! Continue reading to see what we have in store...

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Editor’s Pick: BOI Reporting: A Game of Legal Ping-Pong

For tax professionals trying to guide their clients on Beneficial Ownership Information (BOI) reporting, the last few months have felt like watching a never-ending game of legal ping-pong. Deadlines have been set, overturned, reinstated, delayed, and challenged in court—leaving many businesses (and their advisors) unsure of when, or if, they need to file.

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CTA on Pause! What Tax Pros Need to Know About the Nationwide Injunction and BOI Reporting

On December 3, 2024, a U.S. District Court judge issued a nationwide preliminary injunction prohibiting FinCEN from enforcing the Corporate Transparency Act (CTA) and its associated Reporting Rule. This injunction halts the January 1, 2025, deadline for Beneficial Ownership Information (BOI) reporting, leaving many tax professionals and business entities questioning their compliance obligations. However, this pause is temporary. The government has already filed an appeal, and the injunction could be modified or overturned at any time. FinCEN has acknowledged that reporting companies are not currently required to file BOI reports but may do so voluntarily.

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Tax Scams: What You Need to Know About “Sovereign Tribal Tax Credits”

Tax scams come in many shapes and sizes. Some schemes aim to steal money or identities, while others present as legitimate-looking investment opportunities with promises of reducing tax bills. These offers often come from law firms, investment groups, financial advisors, and even sophisticated organizations. They tempt taxpayers with strategies like inflated art donation deductions, film investments, and even Native American Tax Credits. The IRS advises taxpayers to consult independent tax or legal professionals to avoid falling prey to aggressive promoters. But as tax planners, how do we determine if a strategy is legitimate? Who do we consult so we can understand the difference between a scam and a scheme? Think Outside the Tax Box of course! One popular scheme being whispered about in tax conferences this year is the so-called "Tribal Tax Credits." It’s been a hot topic, with many professionals asking about its legitimacy. Let's dive into the details to better understand this intriguing yet questionable opportunity.

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