Just wanted to mention that you can actually e-file past year returns using some tax software, which is WAY easier than paper filing. I used FreeTaxUSA for my 2020 return when I filed in late 2023. They charge like $20 for past year returns but it was totally worth it to avoid the paper forms nightmare.

I'm going through a very similar situation right now with my 2020 taxes! Lost my job in March 2020 and honestly just couldn't deal with paperwork for the longest time. I finally gathered all my documents last month and realized I might actually owe money despite having taxes withheld from my W-2. One thing that really helped me was calling the IRS Taxpayer Advocate Service (TAS) - they're a separate division that helps people with complex tax problems for free. They don't file your return for you, but they can explain your options and help you understand what penalties you might face. The number is 1-877-777-4778. They were way more patient and helpful than trying to navigate the regular IRS phone system. Also, don't panic about the penalties if you do owe. The failure-to-file penalty stops accruing after 5 months, so it maxes out at 25% of what you owe. The failure-to-pay penalty continues but it's only 0.5% per month. Still not great, but not as scary as it sounds when people say "penalties keep growing forever.

Don't forget that once you move to Japan you'll need to file Form 2555 for the Foreign Earned Income Exclusion! This is huge - it lets you exclude up to $128,750 (for 2025) of foreign earned income from US taxation if you meet either the physical presence test or bona fide residence test.

I went through this exact situation when I married my Korean spouse! A few additional things to consider that I learned the hard way: If you decide to get your wife an ITIN and file jointly, be prepared for the timeline - it can take 7-11 weeks to get the ITIN, and you might need to file for an extension if you're doing this during tax season. Also, make sure to get certified copies of her passport from the Japanese consulate or use an IRS-authorized Certifying Acceptance Agent in Japan rather than trying to mail original documents. One thing I wish someone had told me: if your wife has any financial accounts in Japan with your name on them (even just as a beneficiary), you might need to report those on Form 8938 (FATCA) in addition to FBAR, depending on the account values. The thresholds are different for overseas residents. Also, since you're planning to move to Japan, start keeping detailed records of your time outside the US now. You'll need this for the Foreign Earned Income Exclusion physical presence test. I use a simple spreadsheet tracking entry/exit dates - it's saved me so much headache come tax time! Good luck with everything, and congratulations on your marriage!

One thing nobody has mentioned - have you tried just talking to a human at your old bank? When I had a similar issue, I called and asked to speak with someone in their tax department directly. Explained that the code on my 1099-R was incorrect and potentially subjected me to taxes I didn't owe. Once I got to someone who actually understood tax forms (had to escalate twice), they immediately recognized the error and issued a corrected 1099-R within a week. Sometimes just finding the right person makes all the difference.

I went through almost the exact same situation with my Roth rollover from TD Ameritrade to Schwab in 2022. Got a 1099-R with code 1 instead of code J, and it was a real headache. Here's what I learned: Don't wait around for the bank to fix it if you need to file soon. You can absolutely file your return correctly showing it as a non-taxable Roth rollover on Form 8606, even with the wrong code on the 1099-R. The key is documenting everything properly. I included a statement with my return explaining that the 1099-R contained an incorrect distribution code and that the transaction was actually a qualifying Roth-to-Roth rollover completed within 60 days. Make sure you have your bank statements showing the withdrawal date and the deposit date at the new institution. It took TD Ameritrade about 3 weeks to issue a corrected form after I escalated to their retirement services department, but I had already filed by then. Never heard anything from the IRS about it, so the proper documentation on Form 8606 did its job. The most important thing is not to let the incorrect code scare you into paying taxes you don't owe. A Roth-to-Roth rollover within 60 days is not a taxable event, regardless of what code is on the form.

Be careful with some of these approaches. I tried using the Taxpayer Advocate Service (TAS) route last month during peak filing season, and they've implemented strict case acceptance criteria. Their Internal Revenue Manual (IRM) section 13.1.7.2 specifically prohibits TAS from accepting cases where the taxpayer is simply trying to circumvent normal IRS channels. If your issue doesn't meet their definition of 'significant hardship' under IRC section 7811, you'll be redirected back to the main IRS queue with wasted time.

Last year I had a similar business tax issue and discovered that the IRS Practitioner Priority Service line (866-860-4259) can sometimes be more effective. They typically serve tax professionals, but I've found that if you're prepared, knowledgeable about your issue, and have all your business documentation ready, they often will assist you directly. I was transferred three times but eventually reached someone who resolved my S-Corp filing issue in one call. The key difference from my previous attempts was calling mid-week around 2pm Eastern time.

Has anyone used the TurboTax live expert feature for this kind of situation? I'm having a similar issue and wondering if it's worth the extra cost or if they just tell you generic advice you could find online.

I went through something very similar when I converted my home to a rental property mid-year. The 15-day rule is indeed frustrating, but don't worry - your expenses aren't lost! Here's what I learned after consulting with my CPA: Those $6k in expenses you mentioned are considered "startup costs" for your rental business. Since you didn't rent for 15+ days in 2023, you're right to delete the rental from your 2023 return per the software's guidance. For 2024, when you're actively renting, you have a few options: 1. Add all expenses to your property's basis and depreciate over 27.5 years 2. Make a Section 195 election to deduct up to $5,000 in startup expenses immediately in your first year of business, with the remainder amortized over 15 years The second option could be huge for you since you have $6k in expenses. You'd deduct $5k immediately in 2024 and spread the remaining $1k over 15 years. Make sure to categorize your expenses correctly between repairs (potentially immediately deductible once rental activity begins) versus improvements (must be capitalized). Keep detailed records of everything with receipts and descriptions. The key is that your rental business officially starts in 2024, not 2023, so that's when these rules kick in. Don't let the software trick you into thinking you've lost those deductions forever!