Thanks for this explanation! Yes, the site did take a small fee during the conversion to ETH. Should I be including that fee in my calculations somehow? Sorry if that's a dumb question, I'm still trying to wrap my head around all this.

That fee is important! It should be factored into your cost basis. For example, if you withdrew $1000 worth of winnings but only received $950 in ETH after the fee, your cost basis should be $950, not $1000. When you eventually sell that ETH, you'll calculate your gain/loss based on the $950 figure. The $50 fee isn't deductible separately - it's just part of the transaction cost of acquiring the ETH. This is likely contributing to why your software is showing a capital loss.

How did you figure out the exact price when you received it though? The price can change like every minute and im never sure what exact value to use.

Wait seriously? I had no idea about Form 1096! Is that something I can just download from the IRS website? And does it need to be mailed or can I submit it electronically somehow?

Yes, Form 1096 is required when submitting paper 1099s to the IRS. It's essentially a cover sheet that summarizes all the 1099s you're submitting. You can download it from the IRS website, but it needs to be the official red-ink scannable version - a regular printout won't be accepted. For your situation, you might want to consider e-filing instead. If you e-file your 1099, you won't need the 1096 at all. There are several IRS-approved e-filing services that make the process pretty straightforward, and it's generally faster and eliminates the risk of mail delays. Plus, you get confirmation when the IRS receives your submission.

Does the contractor copy have the same deadline? Like, are you penalized separately for sending it late to the contractor versus sending it late to the IRS?

This is really interesting! I've never heard of a Qualified Disclaimer before. Is this something that can be done even years after being added to a deed? My husband has been on his father's deed since 2002, so about 20 years now. Would it still be possible to do this so close to the sale?

Unfortunately, a Qualified Disclaimer typically needs to be executed within 9 months of when the interest was created or when you turned 21 (whichever is later). Since your husband has been on the deed for around 20 years, this option probably won't work in your situation. There are still other approaches though. One possibility is having your father-in-law give your husband's share back to him as a gift before the sale (though this has gift tax implications). Another is to ensure proper documentation that your husband is acting as a "nominee" owner only. This would require specific language in the closing documents and proper reporting on tax returns.

I used TurboTax Premier last year for a capital gains situation with multiple owners (sold my parents' house where I was on the deed). It handled the basic reporting fine, but I found it didn't ask enough detailed questions about ownership intent or primary residence status for each owner. I ended up having to manually override some entries and add explanatory statements. Unless your situation is very straightforward, I'd recommend at least consulting with a tax professional who specializes in real estate transactions before trying to DIY it.

Thanks for the feedback. That's pretty much what I was worried about. I think I'll use a tax pro this year since the stakes are high, then maybe try software again next year when I don't have such complicated issues.

Actually that's interesting because my partner did have some credit card fraud last year. They had to deal with a bunch of identity theft issues. Do you think that could be causing my tax return to ask for an IP PIN even though we file separately? We've never filed jointly.

Even if you file separately, sometimes these systems can create connections between household members, especially if you've ever shared an address on tax returns. The IRS fraud detection systems are pretty sophisticated and look for patterns across related taxpayers. In your case, it's definitely possible that your partner's identity theft situation triggered additional security for anyone connected to them, including people at the same address. I'd recommend asking your partner if they received an IP PIN and checking with them about any communications they've had with the IRS about identity protection.

This is great advice but setting up an IRS account online is its own circle of hell. They've made the verification process so strict that many legitimate people can't get through it. They asked me for info from a mortgage I had 8 years ago!

Oh wow, I didn't even think about the self-employment tax! This is super helpful - I definitely would have made the same mistake. Do you know if FreeTaxUSA automatically calculates that when you enter 1099 income, or is it something I need to specifically look for?

Yes, FreeTaxUSA should automatically calculate and add the self-employment tax when you enter 1099-NEC or 1099-MISC income that's subject to SE tax. But it's always good to double-check that Schedule SE is included in your forms list before finalizing. The software should walk you through questions about your business expenses too, which can help reduce both your income tax and self-employment tax. Don't forget things like mileage, home office (if applicable), supplies, software subscriptions, etc. Even small deductions add up and can offset some of that SE tax hit.

Good point! FreeTaxUSA's free tier does include Schedule C for business income but might charge for state amendments. Their premium services are still wayyyyy cheaper than H&R Block though.