Has anyone used specific software to track gift card reselling? I'm doing about 15-20 cards per month and manually tracking in Excel is becoming a nightmare, especially when factoring in all the different reward types.

For gift card reselling, you'll definitely want to track holding periods carefully. The IRS does look at how quickly you turn over inventory when determining if this is truly a business activity versus something else. Most legitimate gift card resellers hold cards for at least a few days to a week before selling, which helps establish a clear business pattern. One thing I haven't seen mentioned here is the importance of documenting your business purpose. Keep records showing that you're actively researching market prices, comparing different platforms, and making strategic decisions about when to sell. This helps demonstrate legitimate business activity rather than just quick arbitrage. Also, consider opening a separate business bank account even if you're not formally incorporated. It makes tracking so much easier and provides clear separation between personal and business transactions, which is crucial if you're ever audited. The IRS loves to see clean record-keeping, especially for newer types of businesses like gift card reselling. One more tip: if you're earning significant income from this (over $20K annually), consider making quarterly estimated tax payments to avoid underpayment penalties. The self-employment tax on top of income tax can add up quickly.

Has anyone tried using the consolidated 1099-B summary page instead of entering each transaction? On my Robinhood 1099-B, there's a summary page that shows totals for short-term and long-term transactions.

Another option to consider is FreeTaxUSA - they have a specific nonresident alien version that handles 1099-B forms pretty well for F1 students. I switched from Sprintax last year because their interface for investment income was more intuitive. The key thing I learned is that you absolutely need to track those capital loss carryforwards properly. Even though you can't deduct them against your TA income now, they'll be valuable once you transition to resident status in a few years. I keep a separate spreadsheet with my annual losses so I don't lose track when my status changes. Also, double-check that your brokers reported your transactions correctly as "covered" vs "non-covered" securities. Sometimes there are discrepancies that can affect your tax calculations, especially with wash sales.

Anybody know if it's a problem to efile my regular 2023 taxes while I have a pending amended return for 2022? Don't want to mess anything up further.

Thanks everyone for all the helpful advice! This thread has been a lifesaver. I'm feeling way more confident about tackling this now. Based on what I've read here, I think I'm going to try the e-filing route first since my 2022 return qualifies. If TurboTax keeps giving me issues, I'll check out H&R Block or TaxAct like Ravi suggested. The taxr.ai recommendation from Omar and Chloe sounds really interesting too - having something walk me through exactly what changes with the missing 1099-NEC income would definitely help reduce my stress level. And knowing that Claimyr actually works to get through to the IRS is good backup if I get stuck. One quick question - when you guys e-filed your amendments, did you get immediate confirmation that it was accepted, or does it take a few days? I'm just trying to set my expectations for timing. Really appreciate everyone taking the time to share their experiences. This community is amazing!

Something to consider - if you're paying more than half your mom's support and she qualifies as your dependent, make sure to look into the medical expense deduction too. Since she has dementia, there are probably substantial medical costs. If you itemize deductions, you can deduct medical expenses that exceed 7.5% of your adjusted gross income. This includes costs for diagnosis, treatment, equipment, and even some home modifications if medically necessary. Long-term care services and insurance can also qualify.

I'm dealing with a very similar situation with my father's retirement account that got transferred incorrectly. One thing that really helped me was getting everything documented properly from the beginning. Make sure you have copies of all the original annuity paperwork, the transfer documents, and any correspondence with the insurance company about reversing the ownership. You'll want to keep detailed records of exactly how much of that annuity income goes toward your mother's care - not just the direct deposits to her account, but any expenses you pay on her behalf using those funds. This documentation will be crucial if the IRS ever questions the dependency claim or support calculation. Also, consider talking to an Elder Law attorney if you haven't already. They often have experience with these exact situations and can help you navigate both the tax implications and make sure you're properly set up to handle her finances going forward. Some even offer free consultations for caregiving families. The good news is that once you get the ownership transferred back to her, this shouldn't happen again in future tax years. But definitely get professional help for this year's filing - the dependency claim combined with the income reporting makes this too complex for DIY tax software to handle properly.

My tax guy told me the key is having a completely separate business entity for the 1099 work. If its just you getting paid both ways, the IRS tends to view it as one job. But if you have an LLC or S-Corp for your freelance work that contracts with the company, that creates clearer separation.

The advice about having a separate business entity is solid, but you don't necessarily need to set up an LLC or S-Corp to make legitimate deductions work. What matters most is being able to clearly demonstrate that your 1099 work is genuinely separate from your W2 duties. I'd focus on three key documentation strategies: 1) Keep separate calendars/logs showing when you're doing W2 vs 1099 work, 2) Maintain records of any different clients, projects, or deliverables for your 1099 work, and 3) Track your mileage with specific business purposes noted (not just "went to office"). The IRS will scrutinize situations like yours more closely, but as long as you can show legitimate business separation and aren't just trying to convert regular commuting expenses into deductions, you should be fine. Consider consulting with a tax professional who specializes in mixed employment situations - the upfront cost is usually worth avoiding potential audit issues down the road.