Thanks for bringing this up, but these are both primary residences. We've lived in our current home for 6 years, and the childhood home will become our new primary residence once we complete the purchase. So I think we should qualify for the capital gains exclusion rather than needing the like-kind exchange rules.

You're absolutely right that the primary residence exclusion is your best option here. Since you've lived in your current home for 6 years, you easily meet the 2-out-of-5 years requirement. I mentioned like-kind exchanges just as an alternative for readers in different situations, but your plan to use the Section 121 exclusion for primary residences is perfect for your situation. Just make sure to keep good records of both transactions for your tax files.

I used TurboTax last year for my home sale. It asks all the right questions about how long you lived there and the purchase/sale prices. Just make sure you have all your closing documents handy. The land contract part might be trickier though.

And if the food truck LLC has inventory, you might need to account for cost of goods sold on your Schedule C. This is super important for food businesses since your ingredients and supplies are considered inventory.

I did try contacting them first actually! Their payroll person said they'd "look into it" about two weeks ago but I still haven't received anything. That's why I'm trying to figure out how to work around it in TurboTax since the filing deadline is getting closer.

That's frustrating! If you've already tried contacting them, I'd recommend following up one more time with a deadline - something like "I need this corrected by next Friday to file my taxes on time." Sometimes that creates more urgency. In the meantime, the workaround suggested by others is your best bet. Enter it exactly as shown on the form (so dollar amounts match IRS records) but add detailed notes explaining the discrepancy. The total income reported is what matters most from a tax calculation perspective.

I work with taxes (not a professional, just at a community volunteer center) and see this kind of thing often. Generally, the IRS is concerned with whether all income is reported, not necessarily which box it appears in on a 1099. As long as you include the income and document the discrepancy, it rarely causes problems.

I used TurboTax last year and it handled the 1099-B import fine, but it doesn't really explain wash sales well. It just takes whatever wash sale adjustment your broker reports. If you disagree with your broker's calculation (like OP's situation), TurboTax won't help you figure that out - you'd need to make manual adjustments. I switched to TaxAct this year and it seems to handle it a bit better with more explanations about the wash sale calculations.

Thanks for the info about TurboTax. I'm concerned about the imports because my broker (Fidelity) sometimes categorizes things differently than TurboTax expects. I hadn't considered TaxAct - might check that out instead. Really just want something that will handle the calculations correctly without me having to become a wash sale expert. The whole "substantially identical securities" thing gets really confusing especially with ETFs that have overlap.

Yes, buying in your IRA after selling at a loss in your taxable account does trigger a wash sale! This is a common misconception. If you sell a security at a loss in your taxable account and purchase the same or "substantially identical" security in your IRA (Roth or Traditional) within 30 days before or after, the wash sale rule applies. What makes this particularly painful is that when the loss is disallowed due to an IRA purchase, that loss is essentially lost forever since you can't adjust the cost basis in an IRA.

Does the primary residence exclusion apply to nonresident aliens too? I thought that was only for US citizens and residents.

You're right to question this - the primary residence exclusion actually doesn't apply to nonresident aliens. I should have been more clear about that. While US citizens and resident aliens can exclude up to $250k/$500k of gain on a primary residence, nonresident aliens generally cannot take advantage of this exclusion. However, the reduced withholding rate (10% instead of 15%) for properties under $1 million that will be used as the buyer's residence still applies regardless of the seller's status. This is just for the withholding amount though, not the final tax liability.

Can u file the 8288-B yourself or do u need a tax preparer to do it?