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Something nobody has mentioned yet is that you'll need to be really careful about the 45-day identification period and the 180-day completion period for the 1031 exchange portion. Miss those deadlines and you lose the tax deferral completely. Also make sure your qualified intermediary is bonded and insured - I learned that lesson the hard way when my first QI went bankrupt while holding my exchange funds...
How did you handle the QI bankruptcy situation? Were you able to recover your funds or did you end up having to pay the capital gains?
I was extremely lucky that the bankruptcy happened on day 15 of my 45-day identification period. I immediately hired a new QI who was able to make a claim against the first QI's bond. I did recover about 85% of my funds eventually, but it delayed my purchase of the replacement property and caused a ton of stress. I ended up having to bring additional cash to closing to make up the difference. The bigger problem was that I nearly missed the 180-day deadline for completing the exchange because of all the legal complications. If that had happened, I would have owed tax on the full gain. Now I only use large, established QI companies that have significant insurance and bonding, even if they charge slightly higher fees.
Question for anyone who's done this successfully - what documentation do you need to support the allocation between personal and investment use? Do you just claim 50/50 for a duplex or do you need to measure actual square footage? And what about shared spaces like a basement or driveway?
I did this last year with a triplex (lived in one unit, rented two). My CPA had me use square footage as the most defensible method in case of audit. We calculated the percentage of the total square footage that my unit represented, then allocated purchase price, improvements, and selling costs accordingly. For common areas, we split those proportionally too. Keep VERY detailed records of when you converted part to personal use, any improvements made to either side, and maintenance costs. Take photos of everything. The more documentation you have, the better position you'll be in if the IRS questions your allocation.
An important thing nobody has mentioned yet - look into whether you need to file state taxes as well as federal. Some states consider you a resident even after you move abroad if you haven't established residency elsewhere. What was your last state before moving to the UK? Some states like California and Virginia are notorious for trying to claim expats as tax residents. Also, be aware of FATCA (Foreign Account Tax Compliance Act) requirements. Your UK bank may have already reported your accounts to the IRS, which is why it's important to get compliant with your filings.
This is a really good point about state taxes. I'm originally from California and they kept trying to claim me as a resident for tax purposes for years after I moved to France. I had to provide extensive documentation proving I had no intention of returning to California. Also, the FATCA thing is real - my French bank made me fill out a W-9 form once they realized I was a US citizen, and they definitely report my account information to the US authorities.
California is particularly aggressive about maintaining tax residency. They look for any connection (driver's license, voter registration, family ties, etc.) to claim you're still a resident. Other problematic states include New York, Virginia, and New Mexico. The FATCA reporting is a double-edged sword for expats. On one hand, it means the IRS likely already knows about your foreign accounts, which increases the importance of proper filing. On the other hand, it's caused some foreign banks to refuse US clients altogether due to the reporting burden. It's unfortunately part of the reality of being a US citizen abroad.
Does anyone know if the UK-US tax treaty helps with avoiding double taxation on investment income specifically? I'm also a US citizen in the UK, and while my UK employment income seems covered, I'm confused about how my US-based investments are treated.
The UK-US tax treaty does help with investment income but it's complicated. Generally, you can claim foreign tax credits in the US for taxes paid to the UK on the same income. For US-source investment income like your US investments, you'll typically pay US tax on those first, then declare them on your UK return and get credit for the US tax paid. For dividends specifically, the treaty usually reduces withholding rates. Interest and capital gains have their own rules too. I recommend keeping very clear records of all taxes paid in both countries so you can properly claim credits.
Have you considered bankruptcy? Tax debts CAN sometimes be discharged in bankruptcy contrary to what most people think. If the taxes are more than 3 years old, you filed the returns more than 2 years ago, and the taxes were assessed more than 240 days ago, they might be eligible for discharge in Chapter 7. Even if they can't be discharged, Chapter 13 bankruptcy could force both the IRS and state into a reasonable payment plan based on what you can actually afford.
This is actually not entirely accurate. While some taxes can be discharged in bankruptcy, there are strict requirements. Self-employment taxes specifically have additional complications because they include both income tax and what would normally be FICA taxes (Social Security and Medicare). The FICA portion is much harder to discharge. Also, filing fraudulent returns or willful evasion will prevent discharge regardless of timing. Given that OP deliberately chose not to pay the taxes to fund their business instead, a bankruptcy judge might view that as willful evasion.
I worked for a state tax agency for 8 years. Here's what's happening with your state tax bill: most states have much higher penalty and interest rates than the IRS, and many states (unlike the IRS) compound interest. This is why your state bill has grown more dramatically. For state taxes, I'd recommend requesting a penalty abatement first. Many states have first-time abatement programs similar to the IRS, and some even have hardship programs if you've been in difficult financial circumstances. Don't assume the 10-year rule applies to your state. Some states like California and Kentucky have much longer collection periods (20 years and unlimited, respectively). You need to check your specific state's rules.
Have you considered a 1031 exchange? If you're interested in owning other investment property, you could defer ALL the capital gains taxes by purchasing another investment property of equal or greater value. There are strict timelines though - you need to identify potential replacement properties within 45 days and complete the purchase within 180 days of selling your lake house.
Would the 1031 exchange work even though this was inherited property that I've been using personally as a vacation home? I was under the impression those were only for investment properties.
You're right to question this - a 1031 exchange would not work in your situation. For a property to qualify for a 1031 exchange, it needs to have been held for productive use in a trade or business or for investment purposes. A personal vacation home that's not rented out wouldn't qualify. If you had been renting it out consistently when not using it personally, there might be a partial argument, but from your description, this sounds like a purely personal-use vacation property which wouldn't be eligible for 1031 treatment.
Don't forget about state capital gains taxes too! The federal long-term rate might be 15% for you, but depending on your state, you could owe additional state taxes on the gain. Some states tax capital gains as regular income.
This is so important! I sold property in California last year and was shocked at the additional 9.3% state tax on my capital gains. Nearly doubled my tax bill from what I was expecting.
Carmella Popescu
Another option that might work - have you tried contacting the tax preparer who did your amended return? If you used a professional, they should have kept a copy of everything they filed for you, including the 1040X with the date. If you used tax software, you might be able to log back in and reprint the form.
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Vera Visnjic
ā¢I actually prepared and filed the 1040X myself using paper forms because the amendment was pretty simple - just correcting an education credit amount. So I don't have a preparer to contact. And I do have the physical copy, it's just missing the date in the signature section, which apparently is a deal-breaker for my financial aid office. They're super strict about having complete documentation.
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Carmella Popescu
ā¢That's unfortunate. In that case, I think your best options are what others have suggested - either visiting a Taxpayer Assistance Center in person for immediate help or using one of the services mentioned to get through to the IRS more efficiently. Since you mentioned your deadline is approaching, I'd probably pursue multiple options simultaneously. Start the process with taxr.ai since that seemed to work for someone else with your exact issue, but also try to schedule an in-person appointment at a TAC as a backup plan.
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Kai Santiago
Has anyone else noticed that the IRS seems to be getting even harder to deal with recently? Last year I could at least get through to a person after about 45 mins on hold, but now it's like they don't even pick up at all.
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Lim Wong
ā¢I heard they're severely understaffed and dealing with massive backlogs still. My cousin works for the IRS and says they're processing literally millions of paper forms with too few employees. Apparently the best times to call are early Tuesday, Wednesday or Thursday mornings right when they open.
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Kai Santiago
ā¢Thanks for the tip. Maybe I'll try calling at 7am on Tuesday and see if that helps. It's just frustrating that they make it so difficult to get basic documents that we're legally required to have.
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