This is exactly the kind of complex situation where proper documentation is crucial. A few additional considerations based on your timeline: Since you mentioned the apartment was your primary residence until 2021, make sure you have documentation proving when you moved to the US. The IRS may want to verify the timeline for any potential Section 121 exclusion eligibility, even though you're dealing with a loss. For the cash transport itself, I'd recommend getting a cashier's check or bank draft in Greece if at all possible, even if their banking system is problematic. Many Greek banks can still issue checks drawn on US correspondent banks, which would eliminate the security risks and customs complications of carrying physical cash. It's worth calling a few banks in Greece to explore this option before committing to the cash transport. If you must carry cash, document everything with photos - the original euros before conversion, any exchange receipts, and keep all currency conversion documentation. The IRS will want to see how you calculated the USD amounts for your capital loss, and having clear documentation of exchange rates used will be important. Also consider filing Form 8938 (FATCA) if your foreign financial assets exceeded the reporting thresholds at any point during the year. This is separate from FBAR but equally important for compliance.

Based on your situation, I'd strongly recommend getting professional help given the complexity of international property sales, FBAR requirements, and customs declarations all happening together. A few additional points that might help: **For the cash transport**: Contact the Greek consulate or embassy in your area - they often have updated lists of which Greek banks are still functioning normally for international services. Alpha Bank and National Bank of Greece have historically maintained correspondent relationships with US banks, but you'll need to verify current availability. **Currency conversion documentation**: Keep records of the exact exchange rates you use for converting your purchase price and sale price to USD. The IRS accepts rates from xe.com, oanda.com, or the Federal Reserve's daily rates. Consistency in your rate source is important. **State tax considerations**: Since you mentioned this was your primary residence before moving to the US, check if you established tax residency in your current state before the 2021 sale. Some states have different rules for capital losses from foreign property, and you may need to file amended returns depending on when you actually became a US tax resident. **Backup plan**: Given the amount involved, consider splitting your trip - make one trip to arrange banking/check solutions, then return for the actual money collection. The extra travel cost might be worth it for the added security and compliance simplicity. The documentation requirements everyone mentioned are spot-on, but don't underestimate the value of having everything organized professionally given the multiple agencies involved (customs, IRS, state tax authorities, and potentially FINCEN).

Anyone else notice that the $600 threshold is ridiculously low?? I sold like 5 things from my closet last year and got hit with a 1099-K. Thanks government 🙄

This whole situation is why I keep detailed records of everything I sell online now. I learned the hard way after getting multiple 1099-Ks last year and panicking thinking I owed thousands in taxes. Here's what I wish someone had told me earlier: Create a simple spreadsheet with columns for Item Sold, Original Purchase Price, Sale Price, Platform Used, and Date. For each item, calculate if it's a gain or loss. Most of my old collectibles and electronics sold for way less than I originally paid, so they weren't taxable. The key thing is DOCUMENTATION. Even if you're selling personal items at a loss, you need to be able to prove what you originally paid for them. Save receipts, old credit card statements, even Amazon order history - anything that shows your original cost basis. Without that proof, the IRS might assume your cost basis was $0 and tax the full sale amount. Also, don't stress too much about getting 1099-Ks from multiple platforms. Like others said, it's just reporting - the actual tax treatment depends on whether you made a profit or loss on each item, not which app processed the payment.

This thread has been incredibly helpful! I'm in a similar situation with some REIT shares that have appreciated significantly. One question I haven't seen addressed - does the timing of when you donate the shares to the DAF matter within the tax year? For instance, if I donate the shares in January vs December, does that affect my ability to deduct the full amount? I'm wondering if there are any strategic timing considerations beyond just making sure it happens before December 31st for the current tax year. Also, has anyone dealt with donating shares that pay regular dividends? I'm curious if those dividends continue to flow to the DAF or if they stop once the shares are transferred.

This is exactly the kind of situation where getting professional guidance can save you thousands. While the DAF strategy you're considering is sound, there are some nuances with your income level and the size of this gain that could affect the optimal approach. One thing to consider - since you're already in a high tax bracket with your $650k income, the charitable deduction from the DAF contribution might not provide as much benefit as you'd expect due to phaseouts and limitations. You might want to model spreading the donation across multiple years to maximize the deduction value. Also, with an 8-year holding period, you've got solid long-term capital gains treatment locked in. But consider whether there are any other tax-loss harvesting opportunities in your portfolio that could offset some of the gains from the shares you do sell. This could further optimize your overall tax situation beyond just the DAF strategy.

I'm a regular player on these social casinos and was disappointed to learn these aren't deductible! But it makes sense - I'm basically just buying entertainment. One thing to consider though - if you're a content creator or streamer who plays these games as part of your business, you might be able to deduct them as a business expense. That's what my accountant told me since I have a small YouTube channel where I review social casino games.

This is a great question that comes up a lot! The consensus here is correct - social casino purchases where you can't cash out real money are treated as entertainment expenses, not gambling losses. I've seen people get confused about this because it *feels* like gambling, but the IRS looks at whether there's actual monetary risk/reward. One thing I'd add is to be extra careful about record-keeping if you do have any legitimate gambling activities. The IRS can be pretty strict about documentation for gambling loss deductions, so you want to make sure you're not mixing entertainment expenses with actual gambling losses on your return. Keep those social casino receipts separate from any real gambling records to avoid any confusion during an audit. Also worth noting - if you're spending $2500+ on these games, you might want to consider whether that money could be better invested in tax-advantaged accounts like an IRA or 401k where you'd get actual tax benefits!

Called IRS yesterday - they said standard time is 4 weeks but could take up to 6 if theres any postal delays in your area

I'm in week 4 waiting for my paper check too. Called my local post office and they said there's been unusual delays with government mail in my area due to processing backlogs. Might be worth calling yours to see if there are any local issues. Really wish I had done direct deposit - lesson learned for next year!