Thanks for sharing what worked for you. Did you find that alternating years was financially fair for both of you? And did you need to show this notarized agreement to the IRS, or was it just an agreement between you two?

Alternating years worked out fairly well financially for us. Some years one of us might "lose out" a bit if we had more expenses, but it evens out over time and eliminates the yearly fight. The peace of mind is worth any small financial difference. We've never needed to show the agreement to the IRS because we've stuck to it consistently. It's primarily a document between us to prevent disputes. However, if there ever was an IRS question, having a signed and notarized agreement would help show we had a legitimate arrangement. What matters to the IRS is that only one of us claims the child each year.

I've used Form 8332 for the past 4 years with my ex. It only transfers the Child Tax Credit and the dependency exemption. The custodial parent still gets to claim head of household filing status and the earned income credit if they qualify. The IRS is very specific about this - those benefits stay with whoever the child lives with more, regardless of who claims them as a dependent.

Thanks for clarifying that! That makes more sense now. I was worried I'd be giving up too many benefits, but if I can still claim head of household as the custodial parent, that makes a big difference. I'll look into working out an arrangement with my ex.

Oh man I completely forgot about state taxes! I'm in Minnesota - do you know if they have any special treatment for capital gains or do they just add it to regular income?

Minnesota treats capital gains as regular income and taxes them at your normal state income tax rate. With your income level, you're probably looking at around 7.05% state tax on your gains. So if you're in the 15% federal long-term capital gains bracket, your effective rate is actually more like 22% when you factor in state taxes. It's definitely worth planning for this ahead of time so you don't get surprised by a big tax bill. You might want to consider making estimated tax payments if you're selling a large amount to avoid underpayment penalties.

I've used TurboTax for the past few years with capital gains from stocks and ETFs and it's been fine. Their crypto handling was kinda clunky last year though. If you have a lot of crypto transactions, you might want something more specialized. TT also charges extra for the premier version you need for investments.

Yes! Don't ignore it! I didn't correct some 1099s two years ago (was off by around $500 total) and got hit with a $270 penalty ($50 per form) for "intentional disregard" of filing requirements. Plus one of my contractors got a notice from the IRS because what I reported didn't match his return. Huge headache that could have been avoided.

Thanks for the warning! I had no idea they would actually follow up on relatively small amounts. Guess I better get those amendments filed ASAP. Did you have to pay any additional interest or just the penalty amount?

This happened to me as a contractor! My client issued a corrected 1099 reducing my income by $3k but didn't tell me. I had already filed and paid taxes on the higher amount. Found out months later and had to file an amended return to get my money back. Would have been nice to know immediately!

This is actually exactly what happened - I included some expense reimbursements in their 1099 totals that shouldn't have been counted as income. I'll definitely let them know right away so they don't overpay on their taxes. I really appreciate everyone's advice here. I'm going to start with the corrected forms and make sure I check the "CORRECTED" box, then send copies to my contractors with an explanation. I'll also look into the resources suggested to make sure I get the state filing requirements right too.

This is really helpful advice, thanks! I've been tracking sales but not as formally as you described. Do you have any recommendations for good software or templates to use for this kind of tracking? And do you know if there's a revenue threshold where requirements become stricter?

For your level of business, a well-organized spreadsheet is actually sufficient - that's what I still use. I created columns for purchase date, purchase price, sale date, sale price, platform fees, and profit calculation. I also keep a separate tab for business expenses like software subscriptions. The requirements get significantly stricter once you exceed €22,000 in annual turnover, as you'll lose the Kleinunternehmer status and need to deal with VAT (Umsatzsteuer). Once you hit €60,000 annual profit, you'll need to use double-entry bookkeeping (doppelte Buchführung) instead of simple income-surplus calculation (EÜR). At your current scale, though, the detailed spreadsheet approach should be sufficient for the Finanzamt.

This is such an important point that people miss. My friend got hit with a huge health insurance adjustment bill because he didn't realize his side business income would affect his calculation. The Krankenkasse recalculated two years of premiums retroactively!

Has anyone used the Taxpayer Advocate Service for HSA distribution issues specifically? Just wondering if they're familiar with these types of cases or if I should try the other options first given my tight deadline.

The Taxpayer Advocate Service handles all types of tax issues, including HSA distributions. They're especially helpful when you have a deadline approaching and haven't been able to resolve the issue through normal IRS channels. When I used them for my HSA issue, they were very familiar with the documentation requirements and actually helped me understand exactly what I needed to prove qualified medical expenses. The key with your tight deadline is to call them immediately and emphasize the urgency. They can often place a hold on your account while your case is being reviewed.

I tried this approach last year. Just a heads up that appointments at local IRS offices are often booked out weeks in advance. With only 2 days left, this probably won't work unless you get super lucky with a cancellation.