Real Estate Strategies Archives - Think Outside the Tax Box
By Amber Gray-Fenner, EA NTPI Fellow USTCP

Contracts, Signing Bonuses, and the Substantial Presence Test

In tighter job markets, recruits are often offered signing bonuses (and sometimes moving expenses) to join a firm. Sometimes construction workers temporarily relocate to jobs in other states while they are employed by the company that hired them in their home state. This article reviews some of the foundational tax concepts to consider when evaluating sourcing of income for state tax purposes.

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Fleeing High Tax States And The Stickiness Of Domicile

Part of preparing to leave a high state tax is facing up to the fact that the tax collectors of high-tax states can be kind of clingy. There is more to changing your residence for tax purposes than simple steps like a new driver’s license and a change in voter registration.

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Reflecting On The Conservation Easement Mess

As I write this, the most recent Tax Court opinion on a syndicated conservation easement deal is Jackson Stone South LLC. Good chance there will be another before I finish. Estimates indicate that there are over a thousand docketed cases. Jackson Stone can serve as a pretty good example of how the conservation easement opinions have been going, basically not well for the taxpayers. So we will take a look at it, but mainly I want to look at what tax practitioners have to reflect on.

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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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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

Timing is Everything: A Conversation Between a Tax Pro and Client

The new permanent bonus depreciation regime will bring back the old playbook: lever up to buy a rental property and bonus depreciate everything under the sun. But the tax savvy general partners know that WHEN to depreciate is just as important as how to depreciate.

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Are You a “Real Estate Dealer” or “Real Estate Investor” for Tax Purposes?

Tax law is forever classifying people and making structures that either create benefits or disadvantages on your tax return. Part of getting the most from your return is about understanding the definitions of the IRS. Two that seem very similar but have distinctly different consequences on your taxes, are real estate dealer and real estate investor.

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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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