Don't forget about the primary residence exclusion! If this was your brother's primary residence for at least 2 of the 5 years before the sale, he might qualify to exclude up to $250,000 of gain from his income (or $500,000 if married filing jointly). Based on what you described, he lived there for about 2 years before moving out 2 years ago, so he might just barely qualify if the timing works out exactly. This could potentially eliminate any tax liability from the sale, even if he has to report it.

This is definitely a tricky situation that requires careful documentation. From what you've described, your brother needs to report the sale even though he didn't receive proceeds from the actual sale, because he was still legally on the deed. The key is treating this as a two-part transaction: (1) the original buyout he received when they split up, and (2) the formal sale that just happened. On Schedule D, he should report the sale with his cost basis being the original purchase price plus improvements, and his proceeds being only the buyout amount he received years ago (not the recent sale proceeds). You'll definitely want to include a detailed explanation with the return describing the situation. Also, try to get documentation of the original buyout agreement if possible - this will support your position if the IRS has questions. One important thing to check: make sure you understand whether he received a 1099-S form. If he did, the IRS will be expecting to see this sale reported. If the ex-girlfriend also reports part of the sale, you want to make sure there's no double-reporting of the same income.

Has anyone used tax software to file casualty losses? I'm trying to use TurboTax for mine but it's not very clear on how to enter all this information.

I went through this exact situation after tornado damage to my property last year. One thing that really helped me was creating a detailed inventory with photos for each damaged item or area. For your basement flooding, document everything that was damaged - flooring, drywall, electrical work, etc. - and get separate repair estimates for each category. Since you mentioned you have receipts for $15,700 in repairs, make sure you're separating these by casualty event if the IRS requires it (your two separate storms). Each storm event gets reduced by $100, so you might want to check if combining them or keeping them separate gives you a better deduction. Also, don't forget that you can deduct costs for things like temporary housing, storage, or cleanup that were necessary because of the disaster. I missed claiming some of these expenses initially and had to amend my return. Keep every receipt related to the disaster - even seemingly small expenses can add up! The key thing I learned is that "fair market value" doesn't have to be a formal appraisal for most residential property. Your repair costs, contractor estimates, and before/after photos are usually sufficient documentation for the IRS.

I'm dealing with a similar situation right now! Based on all these responses, it sounds like there are really three main paths: 1) Use a specialized service like taxr.ai that can extract data from your original return PDF and auto-generate the 1040X, 2) Re-enter everything in commercial tax software that supports amendments (like TaxAct), or 3) Fill out the paper forms and mail them in. Given that you only need to add interest income, the automated extraction approach seems most efficient - especially since you already have your accepted return as a PDF. The time investment looks much better than re-entering everything or waiting months for paper processing. Has anyone else used similar automated services for simple amendments like this?

As a tax preparer, I can add some insight to this discussion. For simple amendments like adding missed interest income, the automated extraction services mentioned (like taxr.ai) do handle the cascading calculations properly - when you add interest income, the system will recalculate your AGI, taxable income, and tax liability automatically, just like professional tax software would. Regarding the explanation section on Form 1040X, most of these services do auto-populate basic explanations based on the changes detected. For example, if you're adding a 1099-INT, it might automatically write "Adding previously unreported interest income from [Financial Institution]" in the explanation field, though you can usually customize this. One important tip: make sure you have your original return's AGI handy when using any method, as the IRS uses this to verify your identity during electronic filing. Also, if the missed interest income is substantial enough to trigger additional tax owed, you'll want to include payment to avoid interest and penalties from the original due date. The electronic route is definitely worth the effort over mailing - paper amendments are taking 16-20 weeks to process currently versus 8-12 weeks for electronic submissions.

Does anyone know if I should include my state return in the same envelope as the federal return? TurboTax gave me different addresses for each, but I'm wondering if I can save on postage.

As someone who's helped family members with their first paper filings, I'll add a few practical tips that might save you some headaches: **Before sealing the envelope:** - Make sure you've signed AND dated your return (I've seen people forget the date) - Double-check that your Social Security Number is on every page of your return - If you're married filing jointly, BOTH spouses need to sign **Assembly order I always use:** 1. Form 1040 on top (signed and dated) 2. Any schedules attached behind it (stapled in upper left corner) 3. W-2s and 1099s paper-clipped to the left side (NOT stapled to the return) **One thing that's saved me before:** I always write my SSN lightly in pencil on the back of each W-2. If documents get separated during processing, this helps the IRS match everything back to your return. **Timeline reality check:** Even with tracking, don't expect to see your refund status update online for at least 3-4 weeks. The IRS batch-processes paper returns, so there's an inherent delay before they even start working on individual returns. Good luck with your first filing! The process seems scarier than it actually is.

Are you and your fiancée filing taxes together? Because if so, I think there might be a different issue - you can't claim someone as a dependent if you're filing a joint return with them.

Just to add another perspective - I work as a tax preparer and see this confusion all the time! You're absolutely right that it's the net profit from Schedule C that counts toward the qualifying relative income test, not gross receipts. One thing to also keep in mind is that if you had any estimated tax payments or self-employment tax throughout the year, those don't reduce your "gross income" for dependency purposes - it's still the $2,700 net profit that counts. The self-employment tax is calculated separately and doesn't affect whether you meet the income test. Also, since you mentioned you're getting married next year, just be aware that once you're married, you'll need to decide whether to file jointly (which would be more beneficial in most cases) or separately if one of you wants to continue being claimed as a dependent by someone else. But that's a problem for next year's taxes!