Has anyone used the Medical Expense Statement tool in TurboTax for this? I'm in a similar situation but confused about how to enter my mom's expenses that I paid versus what she paid herself.

Just wanted to add something that helped me when I was in this exact situation last year with my father's medical expenses. Make sure you're tracking not just the obvious medical costs, but also things like: - Medical equipment you bought for them (blood pressure monitors, diabetic supplies, etc.) - Transportation costs to medical appointments (mileage or actual costs) - Prescription glasses and hearing aids - Any dental work you paid for directly I found about $1,800 in additional deductible expenses I almost missed because I was only thinking about hospital and doctor bills. Also, if you're using a Health Savings Account (HSA) or Flexible Spending Account (FSA) to pay for any of their expenses, those don't count toward your itemized deduction since they're already tax-advantaged. One more tip - if you're close to the 7.5% AGI threshold, consider timing some medical expenses. For example, if you know your parents will need dental work or new glasses, paying for it in December versus January could make the difference in whether you get any deduction at all.

Has anyone tried the alternative of using the individual QBI worksheet for each business but then going into the calculation worksheet form and manually overriding the QBI amount? That's what I've been doing, but I'm not sure if it's the "official" approach that ProSeries recommends.

I've been dealing with this same QBI aggregation headache in ProSeries for the past two seasons. What's worked best for me is a hybrid approach combining several of the methods mentioned here. First, I complete each business activity separately in their respective forms (Schedule C, E, etc.) to get the base QBI calculations. Then I use the QBI calculation worksheet override feature to input the aggregated amount, but I also create a comprehensive supporting statement that includes: - The specific election under Reg. 1.199A-4(b)(1) - Detailed business descriptions and how they meet common control/ownership tests - A reconciliation table showing individual vs. aggregated QBI amounts - Clear documentation that this is a software limitation workaround, not a substantive tax position The key insight I've learned is that the IRS doesn't care how your software handles the calculation as long as your tax position is correct and well-documented. I attach this as a PDF statement through the Forms menu, and it e-files without issues. I've had about 15 clients use this approach over two years with zero problems. The documentation takes maybe 30 minutes to prepare once you have a template, which beats the alternative of paper filing or switching software entirely.

I completely understand your frustration - this new $600 reporting threshold has caught so many casual sellers off guard! You're absolutely right that you're not alone in this situation. The key thing to remember is that receiving a 1099-K doesn't automatically mean you owe taxes. You're only taxed on actual profit, not gross sales. Since you're selling personal items at a loss, you likely don't owe any tax on these transactions. However, you can't just ignore the 1099-K since the IRS receives a copy. You'll need to report the income and then show your cost basis to demonstrate the loss. For items without receipts, the IRS does allow reasonable estimates based on original retail prices, especially for personal clothing items. I'd recommend keeping it simple: document your method for estimating costs (like looking up similar items' original retail prices), keep notes on when you purchased items, and be consistent. The IRS understands that people don't typically keep receipts for personal clothing purchases made years ago. Don't panic - this is more of a paperwork hassle than a tax burden since you're not actually profiting. Many tax software programs now have specific sections for marketplace seller income that can walk you through the process.

Maya, I completely understand your panic - I was in the exact same situation last year when I got my first 1099-K from ThredUp and Depop! The good news is that you're absolutely right that you don't owe taxes on losses from selling personal items. Here's what I learned after going through this: You do need to report the 1099-K income, but you can offset it with your cost basis (what you originally paid). For items without receipts, I created a simple spreadsheet listing each item, estimated original cost based on what I remembered paying or could find online for similar items, and noted my estimation method. The IRS Publication 551 actually addresses this - they allow "reasonable estimates" for personal property when exact records aren't available. I documented things like "Coach purse, estimated $300 based on current retail for similar style" or "J.Crew sweater, estimated $80 based on brand's typical pricing." One tip that really helped: check if your credit card or bank has online transaction history going back several years. I was surprised how many clothing purchases I could actually find this way! Also, if you shop at places like Nordstrom or Saks, they often keep purchase history in your online account. Don't stress too much - thousands of us casual sellers are figuring this out together. The key is showing good faith effort to determine your basis, not perfect documentation.

I'm confused about the AMT implications of ISOs. My company is pre-IPO and the shares aren't liquid. If I exercise ISOs, I'll have to pay AMT on the spread between strike price and current 409A valuation, right? But if the company later fails, do I get that AMT back?

This is a great discussion! I want to add some practical perspective as someone who's been through multiple startup equity situations. One thing that's been really helpful for me is creating a spreadsheet to model different scenarios before making decisions. I track: - Current 409A valuation vs my strike price - Projected company valuation growth - My tax bracket and AMT threshold - Cash requirements for different strategies The key insight I've learned is that there's no universal "best" approach - it really depends on your individual situation. For my first startup, ISOs worked great because I could exercise gradually and manage AMT. But at my current company, I went with early exercise + 83(b) because the strike price equaled FMV at grant time, eliminating immediate tax consequences. Also worth noting: if your company offers both restricted stock and ISOs, you might be able to negotiate a mix. I know folks who've gotten 75% ISOs and 25% restricted stock, which gives flexibility for different tax strategies. Don't forget to factor in state taxes too - some states don't have capital gains taxes, which can significantly impact your decision if you're planning to relocate.

I see you're dealing with this on April 15th which adds extra stress! This is definitely a software issue rather than an actual IRS requirement. Since you have a 1095-C (employer coverage) and the Marketplace confirmed you never had their coverage, the problem is somewhere in your tax software settings. Here's what I'd suggest doing immediately: 1) Go to the health insurance section of your return and look for ANY question that might relate to "premium tax credits" or "advance payments" - sometimes these get auto-filled incorrectly, 2) Make sure you're selecting "minimum essential coverage through employer" and nothing related to Healthcare.gov or state exchanges, 3) If you're still stuck, try starting a completely fresh return - sometimes the software gets confused with saved data. Since it's already tax day, if you can't resolve it quickly, consider filing an extension (Form 4868) to give yourself until October to get this sorted out properly. The good news is this is a very fixable problem once you find the right checkbox!

This is such a frustrating situation, especially on tax day! I went through something very similar last year. Since the Marketplace confirmed you don't have a 1095-A on file and you only have employer coverage (1095-C), this is definitely a software error. The key is finding where in your tax software you accidentally indicated you had Marketplace coverage. Look specifically for questions about "premium tax credits," "advance premium tax credit payments," or anything asking if you purchased insurance through Healthcare.gov or a state exchange. Even if you answered the main health insurance question correctly, there might be a secondary question buried somewhere that's still checked "yes" for Marketplace coverage. I'd also recommend clearing your browser cache or restarting the software completely - sometimes these programs glitch and hold onto incorrect information. If you can't fix it quickly today, definitely file Form 4868 for an extension so you have time to sort this out without penalties. You've got this!