Dont forget to check if u need to include any earnings/losses that happened during the recharacterization period too!! When I did mine last yr, the amount that moved from roth to traditional was more than my original contribution because of some gains, and that affected how I reported it on form 8606. turbotax was a bit confusing on this part tbh.

I went through a very similar situation last year and it really is confusing! One thing that helped me was understanding the timeline clearly: since you made the 2023 contribution in 2024 (before April 15) and then recharacterized it in 2024, both actions affect your tax reporting. You'll definitely need to file Form 8606 for 2023 to report the nondeductible Traditional IRA contribution (since that's what it became after recharacterization). The key thing I learned is that the recharacterization is treated as if the money went directly to the Traditional IRA from the beginning - so it never "counts" as a Roth contribution for tax purposes. For your 2024 return, you'll report the recharacterization itself. TurboTax should handle this when you enter your 1099-R information, but make sure you have all the documentation from your IRA custodian showing the proper recharacterization codes. I'd recommend getting your custodian statements that show exactly what happened and when, because the timing and proper documentation is crucial for reporting this correctly. The good news is once you get through this year, future backdoor Roth conversions will be much more straightforward!

Don't forget that healthcare.gov specifically wants your PROJECTED annual income, not just what you've made so far. If you make $3,000 in profits over 3 months, they don't just want to see that - they want to see that projected to $12,000 for the year (assuming steady income). One mistake I made was just submitting my year-to-date income without the annual projection. My documentation kept getting rejected until I explicitly showed the math for how my partial-year income translated to an annual estimate.

For your inventory issue specifically - you're right to think about including that $650 in inventory value. Since you're in a buy/repair/sell business, that inventory represents future income that should be part of your annual projection. The key is to be consistent with your accounting method. If you've been using cash basis (only counting money when it actually comes in/goes out), then your inventory should be valued at what you paid for it, not what you expect to sell it for. If you switch to accrual accounting, you'd count the expected sale value, but then you'd also need to account for all your other income and expenses on an accrual basis. For healthcare.gov documentation, I'd recommend sticking with cash basis but including a line item like "Current inventory at cost: $650 - represents X units expected to generate approximately $Y in future sales over next Z months." This shows them you understand your business has ongoing value beyond just completed transactions. Also make sure your ledger clearly states the time period covered and includes your methodology for the annual projection. Something like "Income projection based on [method] - estimated annual net profit: $X" helps prevent the vague rejection letters you've been getting.

Tbh the IRS doesn't have the resources to audit everyone who got audited b4. They look for specific red flags like unusually high deductions, mismatched income reporting, or math errors. Def make sure ur 1099s match what you're reporting! Also, if ur in the same income bracket as last yr, the DIF score (what the IRS uses to flag returns) might be similar, so double-check everything that got flagged last time.

I understand your anxiety about this! As an independent contractor myself, I went through a similar situation. Here's what I learned from my tax attorney: The good news is that having a prior audit doesn't automatically flag you for another one. The IRS uses statistical models (DIF scores) that primarily look at your current year's return, not your audit history. However, you're right to be extra cautious. Here's what helped me avoid issues after my audit: • Switched to a CPA who specializes in contractor taxes • Keep meticulous records - I now photograph every receipt immediately • Match ALL 1099s exactly (even if they're wrong, report them as received and make adjustments properly) • Be conservative with deductions - only claim what you can fully document The fact that you had to amend suggests there were legitimate errors to fix. As long as your new preparer addresses whatever caused the original audit, you should be fine. Don't let fear prevent you from filing on time - that creates bigger problems! Consider getting a second opinion on your return before filing if you're still worried. Peace of mind is worth the extra cost.

I'd suggest also considering the 95-day rule with capital improvements in a 1031 exchange. If you're buying a replacement property, improvements made within 95 days after closing can be considered part of the exchange value. Might not apply to your situation since you're asking about the relinquished property, but worth noting for the complete picture.

Based on my experience with several 1031 exchanges, the consensus here is correct about splitting your $37,000 in expenses. The $26,000 in capital improvements (roof and HVAC) should increase your adjusted basis on Form 8824 line O since they were substantial improvements that add long-term value to the property. The $11,000 in repairs and maintenance should go on line N as exchange expenses since they were incurred after the property ceased being a rental but were necessary to prepare it for sale. One additional consideration: make sure you have detailed receipts and documentation for all these expenses. The IRS scrutinizes 1031 exchanges more closely, and clear documentation of what constitutes capital improvements versus repairs will be crucial if you're ever audited. Also, since you mentioned the property stopped being a rental 2 months ago, confirm with your tax preparer how this timing affects any final depreciation calculations on the property before the exchange.

11 Has anyone here used owner financing as a buyer rather than a seller? I'm considering purchasing a property this way and wondering about tax implications from the buyer's perspective.

One thing to keep in mind with owner financing is the imputed interest rules. If you're not charging adequate interest on the financed portion (currently around 5.5% for long-term AFR), the IRS may impute interest income to you and treat part of your principal payments as interest income taxable at ordinary rates rather than capital gains rates. Also, make sure your purchase agreement clearly states the allocation of the purchase price if there are any personal property items included (like appliances or furniture). The stepped-up basis only applies to the real property portion, so you want to make sure everything is properly documented for tax purposes. Given the complexity of installment sales with inherited property, I'd strongly recommend getting everything reviewed by a tax professional before finalizing the sale agreement. The tax implications can be significant if not structured properly.