Just wanted to add another perspective on the record-keeping aspect since I've been filing as a professional gambler for 3 years now. Beyond just tracking wins/losses, you really need to document the TIME aspect - the IRS wants to see that you're putting in substantial hours like any other business. I keep a detailed log of hours spent researching teams, analyzing stats, watching games for betting opportunities, and even time spent placing bets and managing my bankroll. Last year I logged over 30 hours per week on average, which really strengthened my case for professional status. Also, don't forget about business expenses you can deduct as a professional: sports data subscriptions, computer equipment, part of your internet bill, even travel expenses if you attend games for research purposes. These deductions can add up significantly and aren't available to casual gamblers. One last tip - consider setting up a separate business bank account and credit card exclusively for your gambling activities. This makes it much easier to track everything and shows the IRS you're treating this as a legitimate business operation rather than just recreational gambling.

This is such a timely post for me! I'm in a very similar situation - made about $52k profit from sports betting last year but my tax forms showed over $400k in "income" which completely messed up my financial aid applications. One thing I learned the hard way is that you really need to start thinking about this early in the tax year, not after the fact. I'm already setting up better record-keeping systems for 2024 based on the advice here about tracking time spent and maintaining business-like documentation. The point about FAFSA is huge - I had no idea that gambling winnings would be reported as gross income rather than net profit for financial aid purposes. It basically made me ineligible for any need-based aid even though my actual take-home was much more modest. For anyone else in this situation, I'd definitely recommend consulting with a tax professional who has experience with gambling income. The rules around professional vs. casual gambling status are pretty nuanced and the stakes are high if you get it wrong.

The 1099-K threshold was supposed to drop to $600 for 2023, but the IRS delayed it again and kept it at $20,000. So you probably won't even get a 1099-K unless you're receiving over $20,000 in Venmo payments. But even if the threshold does change for 2024 taxes (filing in 2025), reimbursements aren't taxable income. Just make sure your Venmo descriptions clearly show these are reimbursements (which it sounds like you're already doing) and keep your spreadsheet as documentation.

As someone who's dealt with similar roommate reimbursement situations, I can confirm that the IRS generally doesn't consider personal reimbursements as taxable income. The key is proper documentation - your spreadsheet tracking is actually perfect for this. A few practical tips from my experience: 1) Keep taking those photos of receipts on your phone before tossing them - it takes 2 seconds and gives you backup documentation 2) Your Venmo descriptions are spot-on - clear labels like "grocery reimbursement" make it obvious these aren't income transactions 3) Consider opening a joint credit card even before marriage if you're comfortable with it - many banks allow this for domestic partners, and it eliminates the transfer issue entirely The 1099-K threshold situation is still evolving, but even if you do receive one, you'll just report it and then offset it as a reimbursement. Your documentation will easily support this if questioned. Don't stress too much about it - the IRS is mainly targeting people hiding business income, not couples splitting grocery bills!

Quick tip for everyone - SAVE YOUR RECEIPTS! I learned this the hard way when I got audited two years ago over my scholarship tax treatment. Make sure you keep: - All scholarship/grant award letters showing amounts and conditions - Course syllabi that list required materials - Receipts for everything you're counting as a qualified expense - Any communication from your school about required equipment The IRS specifically questioned my computer purchase until I showed them the department requirement letter stating all students needed a laptop with certain specifications. Without that documentation I would've been hit with additional taxes plus penalties.

Great discussion everyone! Just want to add one more thing that might help @Giovanni Ricci and others - the IRS has a specific worksheet in Publication 970 (Tax Benefits for Education) that walks you through exactly how to calculate the taxable vs. non-taxable portions of your scholarship. The key distinction is that scholarship money used for "qualified education expenses" (tuition, fees, required books, supplies, and equipment) is tax-free, while money used for anything else (room, board, travel, research, personal expenses) is taxable income. For your specific situation Giovanni - if your program explicitly requires the laptop and software, keep documentation showing that requirement. The $650 in textbooks should definitely qualify if they were required for your courses. The housing stipend portion you mentioned is indeed taxable as you suspected. One tip that saved me headaches: create a simple spreadsheet showing your total scholarship amount, then subtract out each qualified expense with supporting documentation. Whatever's left over is your taxable scholarship income that you'll need to report as "other income" on your tax return.

Does anyone know the deadline for this BOIR thing? I think I have the same situation with my rental property LLC and I've been ignoring all the news about it thinking it didn't apply to me lol

Just wanted to add a quick clarification for anyone else reading this thread - the BOIR filing requirement is based on how your business entity was legally formed, not how it's treated for tax purposes. If you filed Articles of Organization with your state to create an LLC (even a single-member LLC), you generally need to file the BOIR, regardless of whether you're treated as a disregarded entity for taxes and file Schedule C. The sole proprietorship exemption only applies to businesses that operate under your personal name or a DBA without any formal state registration. Also, for those asking about deadlines - LLCs formed before 2024 have until January 1, 2025 to file their initial BOIR. Don't wait until the last minute because the penalties for non-compliance can be up to $500 per day!

Wait a minute - I don't think anyone has addressed the potential drawbacks here. If you give your SSN and they file a 1099-NEC for work that was clearly W-2 employee work (set schedule, supervised work, etc.), YOU could end up paying both halves of FICA taxes (15.3% instead of 7.65%). Before providing anything, I'd send a text saying "Can you explain what tax form you're planning to issue and why?" Document everything. If they say 1099, but you were clearly an employee by IRS standards, you might want to consult with a tax professional. The IRS has specific tests to determine worker classification.

I'd be very cautious about this situation. The timing is suspicious - why wait 8+ months after you stopped working to suddenly request your SSN? A legitimate business would have collected this information when you started working, not months after you left. Before providing any personal information, I'd strongly recommend asking your former employer to provide a written explanation (via text or email) of exactly why they need your SSN and what they plan to do with it. Ask them to specify what tax form they're filing and for which tax year. If they claim they need to issue a 1099 for last year's income, that's potentially legitimate - but they should have done this by January 31st. Late filing suggests poor record-keeping at best, or something more concerning at worst. Also consider that even if they have legitimate tax reasons, you're under no legal obligation to make their life easier after they failed to handle this properly when you were employed. You could simply respond that since no official employment paperwork was ever completed during your time there, you're not comfortable providing personal information now. Remember, you're still required to report this income on your taxes regardless of whether they issue you any forms. But protecting your personal information should be your priority here.