Thanks for bringing this up! Do you have any recommendations for figuring out the specific tax rules for different countries? I'm considering properties in either Portugal or Greece.

For Portugal and Greece specifically, you'll want to look into their "Golden Visa" programs if you're investing enough, as these can offer some tax advantages for foreign investors. Portugal has a decent tax treaty with the US, and they offer a Non-Habitual Resident tax regime that might benefit you. For accurate country-specific advice, I strongly recommend consulting with a tax professional who specializes in expat taxes and has specific experience with those countries. Local property taxes, transfer taxes, and income tax rules vary significantly by country and sometimes even by region within countries. In my experience, spending money on good tax advice before making an international property purchase saved me from some expensive surprises later.

I did one in 2023 and it was definitely complicated but doable. The key was using a qualified intermediary who handled all the details. The hardest part was finding suitable replacement properties within the 45-day identification period in the crazy market. You absolutely need to follow the timelines exactly - no extensions. I almost lost my tax deferral because my closing got delayed, but we pushed hard to get it done just under the wire. But remember, as others mentioned, this won't work for foreign property - has to be US to US.

With FreeTaxUSA, you can absolutely do this! Complete both your federal and state returns in the software, but when you get to the filing stage, only select to e-file your state return. There should be an option to "file state only" somewhere in the filing process. For your federal, make sure you fill out and submit Form 4868 for the extension and pay your estimated amount owed. You can either generate this form through FreeTaxUSA or use the IRS direct pay website to make the payment, which automatically gives you the extension.

That's a great suggestion about the state nonprofit association - I hadn't considered that angle. Do you know if the extension request needs to be submitted in a specific format or to a particular office at the SBA?

The extension request should be submitted through your SVOG portal account under "Correspondence." Include a detailed explanation of your efforts to secure an auditor (with dates and names of firms contacted) and specify how much additional time you need. Be sure to mention that you're specifically struggling to find auditors familiar with Title 2, Subtitle A, Chapter II, Part 200, Subpart F requirements for SVOG grants. Don't wait until the last minute to request this - submit at least 30 days before your deadline if possible. In my experience, the SBA has been reasonable about extensions when you show you're actively trying to comply.

Is that threshold based on the actual awarded amount or the amount spent? My SVOG was for $265k but I only ended up using $248k of it and returned the rest. Not sure if that changes anything regarding the Single Audit requirement.

The threshold is based on the amount expended during your fiscal year, not the amount awarded. So if you only spent $248k of your SVOG funds, you would fall under the $250k threshold and could opt for the simplified compliance audit instead of the full Single Audit requirements outlined in Title 2, Subtitle A, Chapter II, Part 200, Subpart F. Make sure you have proper documentation showing exactly how much was spent and when. This distinction has saved several venue operators a lot of time and money, so it's definitely worth confirming your exact expenditure amount!

How detailed did you get in your non-willful statement? I'm worried about saying too much vs too little. Did you mention specific years or accounts, or keep it more general?

I was pretty specific but concise - about one page single-spaced. I mentioned when I opened each account, why I opened it (moved abroad for work in 2018, needed local banking), and why I didn't know about the reporting requirements (no international tax experience, used regular tax software that never prompted me about foreign accounts). I avoided making excuses but clearly explained my background and why the oversight was genuine. I included specific moments like when I first learned about FBARs and my immediate actions afterward. The IRS seems to appreciate this level of detail as it supports your case for non-willful conduct.

I used TaxAct for my amended returns and then the FinCEN online system for the FBARs. It was doable but required a lot of research. The regular tax software doesn't have great guidance for the Streamlined procedures specifically. If your situation is complex (multiple accounts, business interests, investments), I'd probably get professional help. For basic bank accounts, you might be able to DIY.

How did you come up with that $60-75 figure? Is there a simple calculation to determine the right extra withholding amount?

It's a rough estimate based on the tax brackets. When you have a second job that makes about 25-30% of your main job's income (like the $17k vs $58k in this case), you're typically looking at withholding an extra 22% of the second job's income (since that income is "stacked" on top of your main income and falls into your highest marginal tax bracket). $17,000 × 22% = $3,740 extra tax needed per year. Divide by number of pay periods (usually 26 if biweekly) = about $144 per paycheck. But you can withhold less if your second job is already withholding something, which is why I suggested $60-75 as a starting point. The IRS Withholding Calculator will give you a more precise figure based on your specific situation.

You're correct that it all gets reconciled when you file - you're not evading taxes by having multiple jobs. The issue is just that you might end up with a large tax bill instead of getting a refund. If the amount you owe is large enough (generally over $1,000), you might also face underpayment penalties from the IRS.