Has anyone used the IRS Free File program for back tax returns? My husband is in a similar situation (hasn't filed for 3 years) but we're really tight on money right now.

For your mom's situation with multiple unfiled years, I'd strongly recommend starting with the most recent year (2024) and working backward. The IRS has a general policy of getting taxpayers current first before addressing prior years. Given her income sources - Social Security, pension, and investment income - she likely had filing requirements for most of those years. The threshold for filing when you have Social Security income is much lower than the standard deduction amount. One important thing to consider: if she was due refunds for any of those years, she can still claim them for 2021-2023, but refunds for 2020 are past the 3-year statute of limitations. This could actually work in her favor financially. I'd suggest gathering all her tax documents first (SSA-1099, 1099-R for pension, 1099-DIV/INT for investments) for each year. The IRS can provide wage and income transcripts if she's missing any documents. For someone her age with these income types, working with a tax professional who specializes in unfiled returns would be worth the investment. They can help navigate penalty abatement options and ensure everything is filed correctly the first time.

Just wanted to add some perspective as someone who's dealt with this exact situation. The key thing to remember is that even though it feels unfair (especially when you've put so much money into maintenance), the IRS treats personal vehicles differently than investment assets for good reason - otherwise everyone would try to claim every oil change and car wash as a tax deduction! One thing that might help: keep really good records of any actual improvements (like the backup camera and stereo mentioned above) versus regular maintenance. The distinction can make a real difference in your tax liability. Also, as someone pointed out, the actual tax on $950 probably won't break the bank - long-term capital gains rates are much more favorable than regular income tax rates. If you're still unsure about what qualifies as an improvement versus maintenance for your specific situation, it might be worth the peace of mind to get professional advice or use one of those tax tools people mentioned to make sure you're doing it right.

This thread has been incredibly helpful! As someone who's been putting off dealing with a similar car sale from last year, reading through all these responses finally gave me the clarity I needed. The distinction between improvements vs. maintenance is something I never would have thought about on my own. I actually installed a new exhaust system and upgraded the suspension on my car before selling it - sounds like those might qualify as improvements that could reduce my taxable gain. What really stands out to me is how the actual tax burden might not be as scary as it initially seems, especially with the favorable long-term capital gains rates. Sometimes we get so caught up in the principle of owing taxes that we don't step back and look at the real numbers. I'm definitely going to start keeping much better records for any future vehicle transactions. It's clear that having proper documentation for improvements can make a real difference, and honestly, it's just good practice for any major purchase or sale. Thanks to everyone who shared their experiences and knowledge - this is exactly the kind of real-world advice that's hard to find in generic tax guides!

Just joined this community because I've been dealing with this EXACT same AGI rejection nightmare for the past 10 days! 😭 Reading through all these experiences has been so reassuring - I thought I was going crazy! I've been using my 2023 transcript AGI this whole time (rookie mistake, I know), but after seeing everyone's solutions, I realize I need to: 1. Use my 2022 AGI (not 2023) 2. Find my ORIGINAL 2022 filed return, not the transcript amount 3. Check if the IRS made any adjustments I wasn't aware of I'm pretty sure my 2022 return was adjusted because I remember getting some letter about a missing 1099 that I thought I'd handled, but maybe it changed my AGI. Going to dig through my old TaxSlayer files tonight and see what my pre-adjustment AGI was. If that doesn't work, I'll definitely try the $0 workaround that multiple people have confirmed works. Thank you all SO much for sharing your solutions - this thread is literally saving my sanity right before the deadline! This community is incredible! 🙏

Just created an account to join this discussion because I've been dealing with this EXACT rejection issue for over a week now! 😤 After reading through everyone's experiences, I'm realizing I've been making multiple mistakes: 1. I was using my 2023 transcript AGI instead of 2022 (face palm moment!) 2. I didn't even think to check if my 2022 return had been adjusted by the IRS 3. I've been using the transcript amount instead of my originally filed amount This thread has been incredibly eye-opening! I had no idea there could be a difference between what I originally filed and what shows up on my transcript after IRS adjustments. I'm definitely going to dig through my old TurboTax files from 2022 tonight to find my pre-adjustment AGI. Quick question for the group - if I can't locate my original 2022 tax files (computer crashed last year), would calling the IRS for the original filed AGI be worth the wait time, or should I just jump straight to trying the $0 workaround? I'm getting nervous about the deadline approaching and don't want to waste more time if the $0 method has worked for so many people here. Thank you all for sharing your solutions - this community knowledge is invaluable for us newcomers! 🙏

Has anyone tried just structuring this as a gift instead of a loan? I know there are annual limits but doesn't each person get a lifetime exemption that's pretty high?

Just to add another perspective - don't forget about state tax implications too! Some states have different rules for reporting large cash transactions or loans, especially from foreign sources. In California, for example, they sometimes require additional documentation for large deposits that don't match your reported income, even if it's properly documented as a loan at the federal level. Also, since you mentioned your husband has an LLC, consider which entity should actually take the loan - personal vs business. If the LLC is buying the investment property, having the loan go directly to the LLC might simplify things, but you'll want to make sure the foreign relatives are comfortable lending to a business entity rather than individuals. The rental income and loan repayment structure could also affect your business vs personal tax situation depending on how you set it up.

One thing to keep in mind is that TurboTax's recommendation system is generally pretty solid when it comes to standard vs itemized deductions. The software runs both calculations in the background and automatically selects whichever gives you the lower tax liability (or higher refund). Since you mentioned your itemized deductions were around $15,900 last year and the 2024 standard deduction is $14,600 (single) or $29,200 (married filing jointly), there might be other factors at play. Did you have any changes in your filing status, income level, or maybe some deductions that no longer qualify? Also worth noting that some people find their itemized deductions naturally decrease over time - mortgage interest decreases as you pay down principal, and sometimes charitable giving patterns change. The "sweet spot" for itemizing has definitely shifted upward with the higher standard deduction amounts. If you want peace of mind, you can always manually override TurboTax's recommendation and force it to itemize, then compare the final tax amounts side by side. But in most cases, the software is making the mathematically correct choice for your situation.

Just want to add another perspective here - I'm a tax preparer and see this situation constantly during tax season. The switch from itemized to standard deductions has become incredibly common since the Tax Cuts and Jobs Act significantly increased the standard deduction amounts. What many people don't realize is that it's not just about the dollar amount - it's also about simplicity and audit risk. When you take the standard deduction, there's virtually no documentation required and much lower chance of IRS scrutiny since you're not claiming specific expense categories. For your situation specifically, if you were at $15,900 itemized last year and now the standard deduction is better, you're probably in that "borderline" zone where small changes in your expenses can tip the scales. This is actually a good position to be in because it gives you some control - you could potentially bunch certain deductible expenses (like charitable donations or medical expenses) into alternating years to maximize your benefit. One final tip: keep your itemized deduction records even if you take the standard deduction. You might have large medical expenses or other deductible items later in the year that could change the calculation, and you'll want those records if you need to amend your return.