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Amina Diop
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.
Actually, the IRS delayed it but only for 2023. For 2024 (what we'll file in 2025), the $600 threshold is currently scheduled to take effect, though there's always a chance they'll delay it again. So this is definitely still a concern for next year.
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!
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Zainab Yusuf
Something nobody has mentioned yet - don't forget about education tax credits like the American Opportunity Credit or Lifetime Learning Credit! You can't "double dip" and count expenses paid with tax-free scholarships towards these credits, but if your scholarship doesn't cover all qualified expenses, you might be able to claim a credit for the amount you paid out of pocket. Last year I had a $10,000 scholarship that covered most of my tuition, but I still paid about $4,500 out of pocket for remaining tuition, books and required course materials. I was able to claim the Lifetime Learning Credit for those expenses I paid myself. Made a huge difference on my tax return!
Can you explain more about this "double dipping" rule? If my scholarship is $15k but my total qualified expenses are $20k, can I claim the $5k difference for tax credits?
Zainab Yusuf
ā¢Exactly right! If your total qualified education expenses are $20,000 and your scholarship covers $15,000, you can claim education tax credits on the $5,000 you paid out of pocket. The "no double dipping" rule just means you can't claim tax credits on expenses that were paid with tax-free scholarship money. But any qualified expenses you pay yourself with taxable income (like from a job) can potentially be used for education tax credits. Just make sure you're meeting all the requirements for whichever credit you're claiming - they have different income limits and eligibility rules.
Yara Khoury
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.
How long do you need to keep this documentation? I graduated 3 years ago but now I'm worried about potential audits from my scholarship years.
Sean Doyle
ā¢Generally you should keep tax records for at least 3 years from when you filed the return, but I'd recommend keeping scholarship documentation for 6-7 years to be safe. The IRS has 3 years to audit in most cases, but if they suspect you underreported income by more than 25%, they have 6 years. Since scholarship taxation can be complex and mistakes are easy to make, the longer statute of limitations could apply. Better to hold onto those syllabi and receipts a bit longer than risk not having documentation if questions come up later!
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Ali Anderson
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
Zadie Patel
ā¢The deadline depends on when your LLC was created. If your LLC was created before January 1, 2024, the deadline is January 1, 2025. If your LLC was created in 2024, you have 90 days from the creation date to file. Set a calendar reminder now because the penalties can be steep!
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!
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Yuki Sato
As someone who's been both an employer and worked under the table before, here's what's probably happening: Your former boss is being audited or preparing for tax filing and realized they paid thousands in undocumented labor (you). Now they're scrambling to legitimize those payments by issuing a 1099-NEC. You should definitely report this income on your taxes regardless of whether you get an official form. However, there's a potential benefit here - if they issue you a 1099 now, you might qualify for certain tax deductions related to self-employment that you wouldn't have considered before. Things like a portion of your phone bill, transportation to the job, etc.
Would you recommend the OP ask for a 1099-MISC instead of a 1099-NEC? I've heard the MISC form might have tax advantages in certain situations. Also, does getting a 1099 this late trigger any automatic flags with the IRS?
Yuki Sato
ā¢The employer doesn't really have a choice between 1099-MISC and 1099-NEC for this situation. Since 2020, payments for services performed as a non-employee must be reported on Form 1099-NEC. The 1099-MISC is now used for other types of payments like rent, prizes, medical payments, etc. - not for work performed as an independent contractor. Regarding late filing, it doesn't automatically trigger an audit, but it can raise questions. The employer will likely face penalties for late filing, but that's their problem, not yours. The important thing is that you report the income correctly. Even if you receive the form late, you should still file an accurate return, even if that means amending a previously filed return.
Andre Dubois
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.
CyberSamurai
ā¢This is such a good point that nobody else mentioned! I got hit with this exact situation and ended up owing like $3,500 in self-employment taxes I wasn't expecting. Is there a way for OP to dispute misclassification without creating a huge problem with the employer?
You can file Form SS-8 with the IRS to request an official determination of worker classification, but that process can take 6+ months. A faster option is to file Form 8919 with your tax return, which lets you pay only the employee portion of FICA taxes while indicating you believe you were misclassified. You'd check the box for "reason code G" (worker received Form 1099-MISC or 1099-NEC but believes they should have received Form W-2). This way you're not ignoring the income, but you're also not accepting the higher tax burden of being incorrectly classified as an independent contractor. The employer would still be responsible for their portion of employment taxes. Just make sure to keep documentation showing you were treated as an employee (set schedule, supervised work, used their equipment, etc.).
Emma Davis
I think people are missing an important point about the FAFSA and financial aid applications for grad school. The way your gambling income is reported can HUGELY impact your Expected Family Contribution calculation. When I applied for grad school, my gambling winnings (about $30k profit but $180k reported income) absolutely destroyed my financial aid options because FAFSA saw that massive gross income number. If I had filed as a professional gambler on Schedule C, they would have only seen my net profit. Something to seriously consider if grad school is in your near future!
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Zainab Ibrahim
ā¢That's a really important point I didn't even think about! Do you know if switching to professional gambler status for this coming tax year would help my grad school applications for next fall? Or would they still look at previous years too?
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Emma Davis
ā¢For most graduate program financial aid, they'll look at your prior-prior year tax returns. So for the 2025-2026 academic year, they'll be looking at your 2023 tax returns. For the 2026-2027 academic year, they'll look at your 2024 returns. If you're applying for programs starting Fall 2025, they'll likely use your 2023 returns which are already filed. But if you're looking at programs for Fall 2026, then your 2024 tax filing (which you'll do in early 2025) will be what matters. In that case, switching to professional gambler status for 2024 could potentially help your financial aid situation significantly. Some schools also have supplemental financial aid forms where you can explain special circumstances. If your 2023 return shows inflated income due to gambling winnings versus actual profit, you might be able to explain this situation and provide documentation of your actual net income.
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Daniel Price
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.
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