One more thing on this topic - capital loss carryovers can potentially be used on back-to-back separate and joint returns. Like if you filed as single with carryover losses, then got married, you CAN bring those losses to your joint return. But what's weird is if you file jointly with losses, then get divorced, each spouse gets half the carryover. My ex and I had about $18k in carryovers when we split, and we each took $9k to our separate returns.

For the divorce question about splitting capital loss carryovers - yes, this is covered in IRS Publication 504 (Divorced or Separated Individuals). When spouses who filed jointly get divorced, any unused capital loss carryovers from the joint returns are generally allocated 50/50 between the former spouses on their subsequent separate returns, unless they agree to a different allocation in their divorce decree. However, if one spouse can demonstrate they were responsible for a larger portion of the losses (like if they managed all the investments that generated the losses), they might be able to claim a larger share. But absent specific documentation or agreement, the IRS default is 50/50 split. The key thing is to make sure this gets addressed in your divorce settlement so there's no confusion later when you're both trying to claim the carryovers on separate returns.

One thing nobody mentioned - if you're due a refund for those years, you only have 3 years from the original due date to claim it. So for 2021, you have until April 2025 (since it was due April 2022). After that, you can still file but kiss any potential refund goodbye. If you owe money though, there's no time limit for the IRS to collect, and penalties and interest keep building. So definitely prioritize filing those past returns ASAP.

Hey Liam! I completely understand your stress about this situation - I was in a very similar spot about two years ago when I realized I hadn't filed for 2019 and 2020, and one of my employers had literally disappeared. Here's what worked for me: First, definitely go the IRS transcript route that GalacticGuru mentioned - it's the most reliable way to get your exact wage information. But if you're having trouble with the online verification (like many people do), I'd recommend calling that transcript line at 800-908-9946 early in the morning, around 7 AM. The wait times are much shorter then. While you're waiting for those transcripts, start gathering whatever you DO have - bank statements showing direct deposits, any old pay stubs, even screenshots of your online banking if that's all you've got. The IRS really does prefer that you file with your best available information rather than not file at all. One thing that helped calm my nerves: the IRS is generally pretty reasonable when you're making a good faith effort to comply and file your returns. The scary penalties people talk about are usually for people who just ignore their obligations completely. You're actively trying to fix this, which puts you in a much better category. Also, don't forget to look into penalty abatement options once you get everything filed. If you have a reasonable cause (like unresponsive employers), the IRS might waive some of the penalties. You've got this!

Why not just use Turo? I have 2 cars listed on there and it's way easier than trying to set up your own rental business. They handle all the insurance, payments, contracts, etc. You could still rent to your parents through the platform (which would look more legitimate to the IRS) plus get other customers too. The Section 179 deduction still applies if you're using Turo, but you have to be careful about personal use limits. I think the vehicle needs to be used for business purposes more than 50% of the time.

Based on what everyone's shared here, it sounds like the key is really treating this as a legitimate business from day one. I'd recommend starting with a solid business plan that shows your intent to expand beyond just family rentals - maybe outline how you'll advertise on platforms like Turo, Facebook Marketplace, or even local classified ads within the first 6 months. One thing I haven't seen mentioned is that you'll want to check your state's requirements for car rental businesses too. Some states require special licenses or permits for vehicle rental operations, even small ones. Also, make sure your auto insurance covers commercial rental activity - most personal policies don't, and you could be looking at serious liability issues if something happens during a rental. The documentation piece that Mohammad mentioned about his brother's audit is crucial. I'd suggest keeping a detailed log of every inquiry, rental, and business expense from the very beginning. Even if someone calls asking about rates but doesn't rent, document it. This shows you're actively trying to build a customer base beyond family members. For the Section 179 deduction, remember that's only available if the vehicle is used more than 50% for business purposes. With just monthly rentals to your parents, you might not hit that threshold, so regular depreciation might be your only option initially.

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.

Has anyone used TurboTax for this situation? My daughter and I are in the same boat and I'm wondering if there's a specific tax software that handles dependent students better than others.

I went through this exact same situation with my 19-year-old last tax season! Your son can definitely file his own return while you claim him as a dependent - they're completely separate things. Just make sure he checks the box saying "Someone can claim you as a dependent" on his return. This is crucial because if he accidentally marks himself as independent while you also claim him, both your returns will get rejected and you'll have to deal with a messy correction process. Since he's making around $800-900/month, he'll probably get back most of his federal withholding when he files. And you're absolutely right that you can still claim him and file as Head of Household since you're providing over half his support and he's a full-time student under 24. One tip - if you're both using tax software, make sure you coordinate so there are no conflicts. Some software will automatically assume a working 18-year-old is independent unless you specifically tell it otherwise. Good luck!