Lenders often have some flexibility with the timing, especially if you're proactive in discussing it with them. While they have reporting requirements, they sometimes can work with you on structuring the forgiveness. For example, some lenders might be willing to split a large debt cancellation across two tax years (December/January) if you explain your tax situation. It really depends on the lender and your relationship with them, but it's definitely worth having that conversation well before the planned cancellation.

That's a really helpful suggestion about timing it with medical expenses. I do have some procedures I've been putting off that would probably hit the threshold for medical deductions. Do you know if lenders are usually open to negotiating the timing of debt cancellation? I wasn't sure if I had any control over when they issue the 1099-C.

Good point! Also, some states follow federal insolvency rules and some have their own. I live in California and they have slightly different rules for cancelled debt than the IRS does.

That's a fair point about the amount. My gym is actually $95/month because it has some specialized equipment I use for training. So it would add up to over $1,100 a year, which seems worth deducting if it's legitimate. But I definitely see your point about weighing the potential hassle against the benefit!

$95/month changes things for sure! That's over $1,100 annually, so the tax savings would be more significant. At that price point, it sounds like a premium gym with specific equipment beneficial to your work. Just make sure to document how you use the specialized equipment for referee-specific training. Take photos of yourself using equipment that helps with referee movements, keep a training log showing how your workouts connect to referee requirements, and save any communications from assigning bodies that mention fitness standards. With that kind of documentation and the higher expense amount, the deduction makes more sense.

This is super important advice. The IRS definitely looks at allocation for mixed-use expenses. But how would they even know what percentage you use for business vs personal? It's not like they follow you around the gym...

Wait, I hadn't even thought about state taxes! Thank you for bringing this up. So even though I was only in Texas for a few months as a baby, if it had been a state with income tax, I might have needed to file there too? That's wild! Do you know if there's a similar "streamlined" process for state tax compliance?

You generally only need to worry about state taxes if you have current ties to that state (property, income from there, voting registration, driver's license, etc.). Since you left as a baby and have no connections, most states wouldn't consider you a resident. State tax amnesty programs vary widely by state. If you had been born in a high-tax state like California, you might have needed to address it, but their Voluntary Disclosure Program typically looks at fewer years than the federal program. Again, for your Texas situation, it's not a concern, which is one small piece of good news in this complicated situation!

The exit tax typically applies if your net worth is over $2 million or your average annual net income tax for the 5 years ending before the date of expatriation is more than $172,000 (2021 figure). The $50k investment alone wouldn't trigger covered expatriate status.

Free File Fillable Forms includes Form 7004? I thought those were only available for individual returns like 1040s. Can you really use it for S-corps?

Thanks for the reminder! My S-Corp doesn't have any tax liability (all profits pass through to my personal return), but this is definitely important for C-Corps or S-Corps with certain types of taxes due.

Thanks for this advice! Do we need to do anything special for sales tax collection? The items were sold to buyers in different states.

Good news - you don't need to worry about sales tax collection. eBay now automatically collects and remits sales tax in all states that require it. That's one headache they've taken off sellers' plates in recent years. Just focus on your income tax obligations - reporting the income on Schedule C, deducting your costs and expenses, and paying tax on the net profit. If you continue selling regularly, you might need to make quarterly estimated tax payments, but for a one-time cleanout of old inventory, you'll likely be fine just reporting it on your annual return.

Would it be better to just ignore the 1099-K and not report it? My cousin did that last year and nothing happened.