Would it be better to just use a Roth IRA for this kind of real estate investing? Does UBTI still apply with Roth accounts? Trying to figure out the best structure before I get started.

UBTI rules apply equally to both Traditional and Roth IRAs - there's no advantage to either type when it comes to UBTI taxation. The difference is that with a Traditional IRA, you'll eventually pay taxes on distributions anyway, while with a Roth, you'd normally never pay taxes on qualified distributions. This makes UBTI potentially more disadvantageous in a Roth because you're paying taxes on money that would otherwise grow completely tax-free. However, if the leveraged real estate investment significantly outperforms other potential investments even after UBTI tax, it might still be worthwhile in either account type.

I used the checkbook IRA LLC structure for several years. The UBTI rules still apply exactly the same way - if there's debt-financing involved in the real estate, you'll trigger UBTI regardless of whether it's a direct IRA investment or through a checkbook LLC. The checkbook structure gives you more control over the investments but doesn't change the tax treatment. You'll still need an EIN for UBTI reporting purposes if applicable.

Did you have any issues with trips back to the US during that time? I'm working in France but typically go back to the US for about 3 weeks each year for holidays with family. Worried this might disqualify me.

Short trips back to the US won't disqualify you from bona fide resident status. That's actually one of the main advantages of using the bona fide resident test instead of the physical presence test. I typically spent 3-4 weeks in the US every year visiting family, and it never affected my foreign earned income exclusion eligibility. What matters is that your "tax home" remains in France and that these visits are genuinely temporary. Document that your life is centered in France - your housing, banking, social connections, etc. The IRS understands that foreign residents still visit their home country. Just be careful not to make statements to US officials suggesting you're just "temporarily" overseas, which could contradict your bona fide resident claim.

Yes, I used the streamlined foreign offshore procedures after living in Germany for 3 years without filing. It was fairly straightforward - filed last 3 years of returns claiming FEIE, included a statement explaining my non-willful conduct, and submitted form 14653. No penalties and got everything resolved cleanly.

Did they at least help with setting up your books initially? That's what I'm most worried about - getting started with the right systems.

They did provide initial setup help with QuickBooks, which was somewhat useful. They created a chart of accounts specific to my industry and showed me how to categorize expenses properly for a SMLLC. They also helped set up integration with my business bank account. The issue I ran into was more with ongoing support and inconsistent advice after the initial setup. For just getting your books set up correctly from the start, they might be okay, but you could probably find a local bookkeeper to do that initial setup for much less than their full package price.

I used TurboTax Self-Employed for my single-member LLC last year. It worked fine for me, but my business is pretty simple - just consulting services with minimal expenses. The software walked me through Schedule C and self-employment tax calculations. If your business has inventory, employees, or more complex deductions, you might want more help than just tax software. Also, TurboTax doesn't help with quarterly estimated payments during the year - you'll need to figure those out yourself.

Thanks for sharing your experience! Did your surgeon break down the cost by percentage or did they actually itemize specific parts of the procedure as medical vs. cosmetic? I'm trying to figure out how detailed this needs to be.

My surgeon provided both. The itemized bill showed specific charges for each part of the procedure, and his letter indicated which aspects were medically necessary with a rough percentage estimate. The most important part was his documentation of medical necessity for specific portions. The IRS doesn't require a precise percentage calculation, but they do need sufficient documentation to show what portion was medically necessary versus purely cosmetic. Make sure your doctor clearly explains why certain aspects of the surgery address a functional medical issue rather than just appearance.

Is there any advantage to trying to bunch medical expenses in one tax year rather than spreading them out? Like if I'm having this surgery in January 2025, would it be better to prepay some costs in December 2024?

That's really helpful advice! We do claim education credits each year. Would taking the capital loss deduction potentially mess with those benefits? What should I watch out for?

Generally, lowering your AGI with capital losses is actually beneficial for most education credits since many have income phaseout limits. The American Opportunity Credit starts phasing out at $80,000 for single filers and $160,000 for joint filers, while the Lifetime Learning Credit begins phasing out at $80,000 for single and $160,000 for joint filers. Capital losses that reduce your AGI could potentially help you stay under these thresholds if you're close to them. However, if your income is already low, you should ensure you have enough tax liability for non-refundable credits to be applied against. The AOTC is partially refundable, but the LLC is not refundable at all.

Question - does it matter which lots you sell if you bought the same stock multiple times? Do you have to sell everything or can you pick which purchases to sell?