Does anyone know if there's a certain amount of items you can sell before eBay considers you a business seller? I'm cleaning out my house too but worried about crossing some threshold.

The IRS looks at several factors to determine if you're operating a business rather than just selling personal items: frequency of sales, intent to make profit, time and effort spent, expertise in the items you're selling, and whether you're buying items specifically to resell. From what you've described - clearing out personal items from your house - this sounds like casual sales of personal property rather than a business. However, keep detailed records of everything: what you sold, original purchase price (or good faith estimates), sale price, and all expenses like eBay fees and shipping costs. The $3,200 you've made isn't automatically taxable income if you're selling items for less than you paid for them. But if some items sold for more than your cost basis, that profit portion would be taxable. Also remember that even if eBay sends you a 1099-K, you still need to determine what portion (if any) represents actual taxable income vs. return of your original investment in those items.

Does anyone know if Schedule E passive losses are subject to the SALT cap limitation of $10,000? My tax guy says no because they're "below the line" deductions not itemized deductions, but I'm not 100% convinced.

Great question about Schedule E passive losses! I went through something similar last year with my rental property. One thing I'd suggest is double-checking that your preparer properly classified all your expenses. That $14,500 loss you mentioned - make sure the roof repair was correctly categorized. If it's truly a repair (fixing existing damage), it's fully deductible in the current year. But if it's considered an improvement (like upgrading to a better roof system), it might need to be capitalized and depreciated over time, which would reduce your current year loss. Also, since you're handling the property management yourself, make sure you're documenting your active participation hours. The IRS can be picky about this during audits. Keep records of time spent on tenant communications, property inspections, repair coordination, etc. With your AGI around $95,000, you should definitely qualify for the full $25,000 special allowance, so those losses should flow directly to your 1040 and offset your ordinary income. Just verify that your preparer didn't accidentally trigger any Form 8582 (Passive Activity Loss Limitations) requirements.

Don't forget about state taxes too! Everyone's talking about IRS, but most states also require back tax filing and have their own statutes of limitations. I got caught up on federal but ignored state, and ended up with a nasty surprise from my state tax agency even after the IRS was satisfied.

I went through this exact same situation a couple years ago - the anxiety is real but you're doing the right thing by facing it! Here's what I learned from my experience: The IRS typically wants you to file the last 6 years to be considered "compliant," but like others mentioned, prioritize the last 3 years first if you think you're owed refunds. I discovered I was leaving over $4,000 on the table from 2020-2022 that I almost lost to the 3-year deadline. One thing that really helped me was requesting my "wage and income transcripts" from the IRS for each year I missed. This shows you exactly what income was reported to them (W-2s, 1099s, etc.) so you know what they already know about. It helped me realize I was missing some 1099s I had forgotten about. For someone with mainly W-2 income like you described, the returns should be pretty straightforward. I used TurboTax for prior years and it walked me through everything. The penalties weren't as scary as I thought they'd be, especially for years where I was due refunds. Start with 2021-2023, get those refunds secured, then work backward. You've got this!

Does anyone know if you have to pay this collectible tax rate if you inherited items? My grandfather left me his coin collection and I'm thinking about selling some of it.

One thing to keep in mind about those vintage comic books you mentioned - the condition and authenticity can massively impact both the sale price and your tax liability. If you're dealing with valuable comics, make sure you keep detailed records of what you paid originally (your "basis") including any restoration or grading costs you might have incurred, since those can be added to your cost basis. Also, if you're planning to sell multiple comics over time, consider the timing. Since collectibles are taxed at your ordinary income rate (up to that 28% cap), selling them in a year when your other income is lower could save you money. For example, if you have a year where you're in the 12% bracket instead of 22%, you'd pay 12% on the collectible gains instead of 22%. The IRS can be pretty strict about hobby vs. investment classification too. If you're buying and selling comics regularly, they might consider it a business rather than capital gains, which would change how everything gets taxed. Keep good records of your transactions!

I know this is slightly off topic, but which medical studies are paying so well? I've only been finding ones that pay like $50-100 for a day of testing, and you made $5,800? Are you doing pharmaceutical trials or something more involved?

I'm a tax professional and can confirm that your medical study income on 1099-MISC forms absolutely qualifies as earned income for Roth IRA contributions. The IRS considers compensation for your time, participation, and following study protocols as "payment for services rendered," which falls squarely under the earned income definition. The key test is whether you're being paid for your active participation versus just receiving reimbursement for expenses. Since you're undergoing tests, taking medications, attending appointments, and following specific protocols, you're clearly providing services that warrant compensation. A few important points to remember: - This income is subject to self-employment tax (15.3%), so plan accordingly - You'll need to file Schedule C to report this business income - Keep records of any unreimbursed expenses related to your participation (travel, parking, etc.) as these may be deductible - The $6,500 Roth IRA contribution limit for 2024 still applies regardless of your total earned income Your $5,800 from medical studies gives you plenty of room to make a substantial Roth contribution this year. Just make sure to set aside funds for the additional taxes you'll owe on this self-employment income.