Is anyone using TurboTax for this issue? I'm wondering if the software can handle this situation properly or if I need to go to an actual tax professional.

This is a really common issue now with the new 1099-K reporting thresholds. I went through something similar last year with my DraftKings deposits through Venmo. The key thing to understand is that the 1099-K doesn't mean you owe taxes on the full amount - it's just reporting gross receipts. For your situation, you'll need to report the gambling winnings as income on Form 1040, Schedule 1, line 8b. But here's the important part - you can deduct your gambling losses up to the amount of your winnings as an itemized deduction on Schedule A. Since you mentioned being down $3,000 overall, this deduction is crucial. The biggest challenge is documentation. Start gathering everything now - bank statements, screenshots of your betting account history, transaction records from the gambling sites, etc. The IRS expects detailed records of both winnings AND losses. I learned this the hard way when I got audited. One tip: don't just rely on the Venmo transactions. Get your actual win/loss statements directly from the gambling sites if possible. Those are much more detailed and credible for IRS purposes.

Don't forget about the Earned Income Tax Credit! If you're a stay-at-home parent with 3 kids and only one income, the EITC can be substantial. Getting married might change your eligibility or the amount you receive. When we were making around $80k with 2 kids, we found that staying unmarried actually gave us a bigger combined refund because of how the EITC worked for us.

I'm in a very similar situation and just went through this analysis myself! One thing that really helped me was using the IRS's own withholding calculator at irs.gov to compare scenarios. It's free and official, so you know the calculations are accurate. With your income level ($95k) and 3 kids, you're likely to benefit from marriage because: 1) The Child Tax Credit ($2,000 per child) has higher income phase-out thresholds for married filing jointly 2) Your boyfriend's Head of Household status is good, but Married Filing Jointly standard deduction for 2024 is $29,200 vs $21,900 for HOH 3) The mortgage interest deduction he gets from the home purchase will still benefit you both when married However, definitely check if you're currently receiving any means-tested benefits like SNAP, WIC, or Medicaid. Sometimes the tax savings don't outweigh the loss of benefits. I'd also suggest running the numbers for both 2024 AND 2025 tax years, since some credits and thresholds change annually. We found that while marriage helped us in 2024, it might not be as beneficial in 2025 due to some expiring provisions. Good luck with your decision!

Quick question for anyone using OLT for non-resident filing - does it handle multiple 1099s? I have one from Robinhood, one from Webull, and another from TD Ameritrade (all with different wash sales and dividends). Wondering if I need to combine these somehow or if the software can handle multiple investment accounts.

As someone who's navigated the non-resident alien tax maze with investment income, I feel your pain! Here are a few additional tips that might help: 1. **Double-check your substantial presence test** - Make sure you actually qualify as a non-resident alien for tax purposes. Sometimes students think they're non-resident when they might actually be resident aliens for tax purposes after being in the US for multiple years. 2. **Consider the treaty benefits** - Depending on your home country, there might be tax treaty provisions that could reduce your tax liability on investment income. Check if your country has a tax treaty with the US. 3. **Keep detailed records** - Document all your trades, especially the wash sale transactions. The IRS may ask for supporting documentation, and having everything organized will save you headaches later. 4. **State tax considerations** - Some states don't tax non-resident investment income at all, while others have different rules than federal. Research your specific state's requirements. The Free File options mentioned above are definitely worth trying first given your budget constraints. If those don't work out, you might also check if your university's international student services office has any tax preparation assistance or recommendations for affordable services that specialize in non-resident returns. Good luck with your filing!

I'm actually an enrollment services staff member at a university (not tax advice!!!) but I can explain why Box 7 exists. Schools often collect spring semester tuition in December of the previous year. So for spring 2026 classes that start in January, students might pay in December 2025. Box 7 is checked to let you know some of the money reported in Box 1 is for classes that start in the following year. The IRS typically wants you to claim education expenses in the year the classes actually occur, not necessarily when you paid. You should request an account statement from your university showing exactly which charges and payments were for which specific semesters. That's the best documentation for sorting this out!

Just wanted to add another perspective as someone who's dealt with this Box 7 situation multiple times. The key thing to remember is that you need to match your education expenses to the actual academic periods, not just when you paid. I keep a simple spreadsheet each year tracking: - Payment date - Amount paid - Which semester/term it was for - Academic period start/end dates This makes it much easier when tax time comes around, especially with Box 7 situations. You can then clearly see which portions of your payments were for classes that actually occurred in the tax year you're filing for. For your $8,750 situation, if you can get that breakdown from your university showing which portions were for 2025 classes versus future terms, you'll have exactly what you need for Form 8863. Don't let Box 7 scare you away from claiming legitimate education credits - just make sure you're only claiming the portion that actually applies to 2025!

Don't forget about potential state tax implications too! What state are you in? Some states have different rules for married couples vs single filers than federal.

Another thing to consider is the timing of when you actually tie the knot! Since the IRS looks at your marital status on December 31st, even if you get married on December 30th, you'd be considered married for the entire tax year. This could work in your favor for maximizing your 2025 tax benefits. Given your situation - $95k income, 3 kids, stay-at-home parent, and new home purchase - you're likely looking at significant savings by filing married jointly. The combination of higher standard deduction, better utilization of child tax credits, and potential mortgage interest deduction benefits should outweigh any potential downsides. One practical tip: if you do decide to get married this year, make sure to update your partner's W-4 with their employer right after the wedding. They'll likely want to adjust their withholdings since the tax brackets and calculations will be different as a married couple. This can help avoid any surprises at tax time!