Thanks for this! I'm a bit confused though - when I file the amended return for my 2023 taxes to claim the AMT credit I missed, do I also need to file Form 8801 for my 2024 return to track any unused credit? Or does the amended 2023 return take care of everything?

You'll need to file Form 8801 with your 2024 return to calculate how much of your AMT credit from 2023 you can use in 2024. The amended 2023 return establishes that you paid AMT and are entitled to the credit, but it doesn't automatically apply that credit to future years. Think of the amended 2023 return as creating the credit, and Form 8801 on your 2024 return as using (or tracking) that credit. If you can't use the entire credit in 2024, you'll file another Form 8801 with your 2025 return, and so on until you've used up the entire credit.

TurboTax Premier and above do handle AMT credits and carryforwards if you use it consistently year to year. The key is importing your previous year's return so it can pull in the AMT information. In your first year claiming the credit, you may need to manually enter some information from your prior year return if you didn't use TurboTax before.

Thanks for mentioning Form 8283. My donation was actually just a wire transfer though - it wasn't a non-cash donation. Would I still need that form? And what about the appraisal requirement?

For a cash donation (like your wire transfer), you won't need Form 8283 or an appraisal - those are only for non-cash donations like property, stocks, artwork, etc. For your cash donation, you'll need a receipt or acknowledgment letter from the organization that includes: the organization's name, the amount donated, the date of the donation, and a statement that no goods or services were provided in exchange for the donation. Since your donation is over $250, this written acknowledgment is absolutely required by the IRS.

TurboTax works fine but you have to manually enter the charity as "Other" and then fill in all the details yourself. The software won't verify if the organization is actually eligible for deduction though - that research is on you.

Wait, so I need to file both Form 1098 AND Form 1099-INT? That seems redundant. Couldn't I just file one of them? And regarding the amortization - our agreement does specify an interest rate (5%), but not exactly how much of each payment is principal vs interest. Does that mean I need to create an amortization table?

Yes, you may need to file both forms as they serve different purposes. Form 1098 reports mortgage interest that the borrower has paid to you, which they can potentially deduct. Form 1099-INT reports interest you've paid to someone else. However, in your specific case, since this is mortgage interest being received by you (not interest you're paying out), you likely only need Form 1098, not 1099-INT. I apologize for the confusion. Since your agreement specifies a 5% interest rate but doesn't break down each payment, you should definitely create an amortization table. This will help you properly track how much of each payment is interest versus principal reduction. You need this to accurately report your interest income and to provide correct information to your family member for their potential deduction. Most spreadsheet programs have templates for creating these tables.

This is a really good point about installment sales! I did a seller-financed deal last year and completely missed filing Form 6252. Had to file an amended return. The property was actually a rental I sold to a tenant, so I had depreciation recapture to deal with too. That's a whole other can of worms!

Have you ever been audited? I'm terrified of claiming professional gambler status and then getting slammed by the IRS. What kind of documentation do you keep to prove you're a pro?

I haven't been audited, but I'm prepared if it happens. I keep extensive records: a daily log of hours spent researching and betting, all transactions (wins AND losses), a business plan, separate bank accounts for gambling activities, and spreadsheets tracking performance by sport/bet type. The key is consistency and business-like conduct. I bet year-round, not just during certain seasons. I have evidence of pursuing expertise (subscriptions, courses, etc.). I can demonstrate that I approach this methodically, not just as entertainment. The IRS looks at factors like regularity, expertise, time committed, and whether you depend on the income. It's definitely not for casual bettors, but if you're serious and methodical about it, professional status can make financial sense.

This happened to me too! The IRS compared the W-2G from the casino (showing just the wins) without considering my losses. Such a nightmare to fix.

Is there a minimum amount that sportsbooks report to the IRS? I won about $3k total this year across DraftKings and FanDuel but haven't received any tax forms from them.

Does anyone know if this would be different if I was selling things regularly? Like I sell my old electronics every year when I upgrade. Does that make it a "business" for tax purposes?

The distinction between hobby/personal sales and a business depends on several factors, not just frequency. The IRS looks at whether you're trying to make a profit, how much time you spend, how you conduct the activity, and if you depend on the income. If you're just selling your own used personal items (even if you do it yearly), that's generally not a business. You're just recouping some value from your personal property, especially if you're typically selling at a loss compared to what you paid. However, if you start buying items specifically to resell at a profit, that crosses into business territory.

I got a letter from the IRS last year about "unreported income" from a 1099-K. It wasn't a full audit, but I had to explain that it was from selling personal items at a loss. They accepted my explanation after I provided some documentation, but it was still stressful.