So what happens if you don't do the improvements within the 180 days? Do you lose the entire 1031 benefit or just the portion related to the improvements?

If the improvements aren't completed within the 180-day exchange period, only the actual completed improvements can be counted as part of the exchange. Any unused funds held by the QI for incomplete improvements would be considered "boot" and returned to you - and you'd owe taxes on that portion. You wouldn't lose the entire 1031 benefit, just the tax deferral on the portion that wasn't properly used within the timeframe. For example, if you earmarked $50,000 for improvements but only completed $30,000 worth within the 180 days, you'd owe taxes on the $20,000 difference. That's why it's crucial to be realistic about what improvements can actually be completed in that timeframe.

I did a reverse exchange last year. It's definitely more complex and expensive than a standard exchange, but doable. You'll need an Exchange Accommodation Titleholder (EAT) to take title to the new property while you sell your relinquished property. Expect to pay about twice as much in fees compared to a standard exchange. Make sure you have very secure financing lined up because you'll essentially be carrying both properties until your original one sells. The same 180-day rule applies - you must sell your original property within 180 days of acquiring the new one. I cut it close (sold on day 168) and the stress nearly killed me!

What if some of my HSA contributions were made directly by me (not through payroll)? I contributed $3,000 through my employer and then added another $2,000 on my own to max out the individual limit.

For contributions you made directly (not through payroll), those should definitely show up in the tax breaks section. In TurboTax, those direct contributions should be entered in the HSA section specifically, not as part of your W-2 entry. Those contributions will appear on Form 8889 Line 2 as "contributions made to your HSA" and will become an above-the-line deduction on your Form 1040 Schedule 1. This reduces your adjusted gross income directly. You should see these contributions reflected in your tax breaks section because they're giving you an additional deduction beyond what was already excluded from your W-2 wages.

Hmm, that's a good point - I need to check if I accidentally entered them twice. I know for sure I entered them during the W-2 section, but I can't remember if I also entered them again in the HSA section. I'll go back and review. Thanks for the tip!

Thanks for this perspective. I hadn't considered the "round-trip transaction" angle. If I were to actually relocate and live abroad full-time (which I'm planning to do anyway), would that strengthen the legitimacy of this arrangement at all? Or would the IRS still view the structure itself as problematic regardless of my residency?

Actually living abroad full-time would certainly help satisfy the physical presence test for the Foreign Earned Income Exclusion, but it wouldn't necessarily legitimize the overall structure. The IRS would still question why this particular business arrangement is necessary. They'd look at factors like: Does this foreign management company have any employees besides you? Does it manage properties for anyone else? Is the fee structure comparable to what unrelated property management companies charge? Does the company have legitimate business operations in the foreign country?

Is that the same as the GILTI tax stuff I keep hearing about with foreign corporations? I thought that made foreign corps less attractive after the 2017 tax law changes.

Thanks for mentioning this! I hadn't even thought about retirement accounts. Is one better than the other between SEP IRA and Solo 401(k)? And can I still contribute for 2024 or is it too late?

Solo 401(k) generally allows higher contributions when your income is lower because it has both an "employer" and "employee" contribution component. SEP IRAs are simpler to set up but only allow the "employer" contribution. For 2024 contributions, you can still open and fund both types until your tax filing deadline (including extensions). So if you file for an extension, you could potentially contribute all the way until October 15, 2025 for the 2024 tax year. That gives you plenty of time to figure out exactly how much you can afford to contribute once you know your full 2024 income.

I've used both methods. For my small apartment office (about 100 sq ft), the simplified method gave me $500 deduction ($5 × 100). When I calculated actual expenses (rent percentage, utilities, etc.), it came to nearly $2,200! Definitely worth tracking real expenses if your rent/mortgage is high.

What about the "Covered/Uncovered" designation on the Stash form? Mine has both types of transactions and I'm not sure if that affects how I enter them.

The "Covered/Uncovered" designation is directly related to whether the cost basis was reported to the IRS. "Covered" securities (typically those purchased after 2011) have their cost basis reported to the IRS by Stash, and these usually correspond to the Code D transactions I mentioned. "Uncovered" securities don't have their cost basis reported to the IRS by the broker, so you're responsible for calculating and reporting the correct cost basis yourself. For these, you'll need to enter the purchase information manually and keep good records in case of an audit. TurboTax has separate entry sections for covered and uncovered securities, so make sure you're entering each transaction in the correct section.

Foreign tax paid usually goes in the Foreign Tax Credit section, not directly on the 1099-B entry screens. In TurboTax, after you finish entering all your 1099-B info, look for a section about foreign taxes or foreign tax credit. Even small amounts should be entered because they're directly creditable against your tax bill.