Has anyone used FreeTaxUSA for reporting investments? H&R Block and TurboTax want to upgrade me to paid versions once I mention having a 1099, but I'm trying to save money.

Don't stress too much! Your situation is totally manageable. With only $3,800 invested and around $290 in gains/dividends, this is exactly the kind of straightforward investment income that tax software handles really well. Here's what I'd recommend: stick with TurboTax since you're already familiar with it, but you'll need to upgrade to at least the Deluxe version to handle investment income (the free version won't support 1099 forms). The upgrade is usually around $40-60, which is still way cheaper than hiring a CPA for such a simple situation. The consolidated 1099 will have clearly labeled boxes - you'll mainly be looking at dividends (both ordinary and qualified) and any capital gains/losses from your stock sales. TurboTax will ask you simple questions like "Do you have investment income?" and then walk you through entering each relevant box from your form. Since you mentioned Robinhood in the comments, that's great news - they definitely support direct import with TurboTax, so you won't even need to manually enter the numbers. Just connect your account and let the software pull everything over automatically. For someone in your situation (hospital worker with simple finances plus small investment activity), this should add maybe 15-20 minutes to your normal tax prep time. You've got this!

Has anyone used TurboTax for handling a mixed rental/primary residence? Does it handle the expense allocation well or should I use a different tax software this year?

One thing I haven't seen mentioned yet is the potential home office deduction. If you use part of your home exclusively for managing your rental properties (like a dedicated space for keeping records, communicating with tenants, handling bookings), you might be able to claim a home office deduction on top of your rental property deductions. Also, be extra careful about the "personal use" test for the Airbnb portion. If you or your family use those rooms for personal purposes for more than 14 days per year OR more than 10% of the days they're rented at fair market value, whichever is greater, it could affect how you report that income and what expenses you can deduct. This is different from the long-term rental rooms where personal use rules are more straightforward. Keep detailed records of everything - dates of occupancy, cleaning receipts, maintenance costs, utility bills. The IRS pays extra attention to short-term rental activities, so good documentation is crucial.

This is definitely a tricky situation! I'd recommend being very cautious here. Even if the IRS made an error, you could still be on the hook for penalties and interest if you spend money that wasn't rightfully yours. Here's what I'd do in your shoes: 1. Don't cash the check immediately - deposit it into a separate savings account that you won't touch 2. Get your 2022 account transcript as others suggested to see all payments/credits 3. Review your 2022 tax return AND any amendments you filed - look specifically at estimated tax payment lines 4. If you used a tax preparer or accountant, contact them to review your records The fact that you had K-1s and amendments makes this more complicated. Sometimes estimated payments get applied incorrectly between tax years, or there can be duplicate reporting of payments on amended returns. I'd also suggest keeping detailed records of all your communications with the IRS about this issue. If they do come back later claiming it was an error, having documentation of your good faith efforts to resolve it could help with penalty abatement. Better to be safe than sorry with a $12k+ situation!

I'd be very cautious about this situation. Large unexpected refunds from the IRS are often errors, and you could be held liable for repayment with interest and penalties even if it wasn't your mistake. Before doing anything with that check, I'd strongly recommend: 1. **Get your account transcripts immediately** - both the regular account transcript AND the wage & income transcript that shows third-party payments. You can request these online at irs.gov or by calling 800-908-9946. 2. **Review ALL your 2022 tax documents** - your original return, any amendments, and especially look at estimated tax payment lines. With K-1 complications and multiple amendments, it's easy for payments to get double-counted or misapplied. 3. **Contact your tax preparer** if you used one - they may have records of payments made on your behalf that you've forgotten about. 4. **Don't spend the money yet** - deposit it in a separate high-yield savings account and don't touch it for at least 6-12 months. The IRS generally has 2 years to recover erroneous refunds. 5. **Document everything** - keep records of all your communications with the IRS about this issue. If they do come back later, showing good faith efforts to resolve it can help with penalty abatement. I've seen too many cases where people spent unexpected refunds only to face demands for repayment plus penalties later. Better safe than sorry with $12,500!

I made a similar mistake last year with my daughter's 529. What we should have done: 1) Use the 529 for qualified education expenses (tuition, books, etc.) 2) Then separately contribute to the Roth IRA from regular funds Instead, we did what your dad did and created a tax headache. We ended up having to pay taxes on the earnings portion of the 529 distribution plus a 10% penalty. And then we had to make sure my daughter had enough earned income to justify the Roth contribution.

This is a really complex situation that trips up a lot of people! Based on what you've described, here are the key issues you need to address: 1. **The 529 Distribution (1099-Q)**: Since you received the 1099-Q in your name, you need to report this distribution. If the $8,400 wasn't used for qualified education expenses, you'll likely owe income tax on the earnings portion plus a 10% penalty. 2. **The Roth IRA Contribution**: This is a separate transaction. Even though your dad provided the funds, if the money went into YOUR Roth IRA, it counts as your contribution. You can only contribute to a Roth IRA if you have earned income (from a job) that's at least equal to your contribution amount. 3. **Gift Tax Considerations**: Your dad giving you money to put in the Roth IRA is technically a gift. You won't owe taxes on receiving it, but he might need to file a gift tax return if it exceeds the annual exclusion limit. My recommendation: Consider consulting with a tax professional for this year since you have multiple moving parts. For future reference, it's much cleaner to use 529 funds directly for education expenses and fund retirement accounts separately with earned income. The new SECURE 2.0 rules mentioned by others will make 529-to-Roth transfers easier starting in 2024, but unfortunately don't help with your current situation.

Has anyone dealt with this situation but with an unmarried couple? My girlfriend and I bought a house last year (both names on mortgage and deed) but I pay 75% and she pays 25%. The 1098 has both our names. Are the rules the same for us as they are for married couples filing separately?

Just to add some additional context that might be helpful - when you're documenting your 60/40 split, make sure you keep records of not just the mortgage payments themselves, but also any related expenses like PMI (private mortgage insurance) if applicable. Those can also be split proportionally based on your contribution percentages. Also, don't forget about the SALT (State and Local Tax) deduction limit of $10,000 if you're itemizing. If your property taxes plus state income taxes exceed this limit, you'll want to strategically plan which spouse claims what portion to maximize your combined tax benefit. Sometimes it makes sense to have one spouse claim the full property tax deduction while the other takes more of the state income tax deduction, rather than splitting everything proportionally. Keep detailed records of all your payments and consider setting up a simple spreadsheet to track the percentages throughout the year - it'll make next year's filing much easier!