I'm actually going through something similar with a different payroll service. What happens if you don't get this resolved before the filing deadline? Is it better to file an extension or try to file with the substitute form?

I went through this exact situation with my S-Corp a few years back when my payroll company went out of business mid-year. Here's what I learned from my CPA and the IRS: 1. **Document everything** - Keep records of all your attempts to contact Gusto, including dates, times, and what they told you. Screenshot any emails or chat conversations. 2. **Know your rights** - As others mentioned, Gusto has a legal obligation to provide your W-2 regardless of your subscription status. The fact that they processed payroll for you creates this responsibility. 3. **Form 4852 is your friend** - If Gusto continues to refuse, Form 4852 (Substitute W-2) is the legitimate IRS-approved solution. Make sure to use your final paystub's year-to-date totals, as these should match what was reported to Social Security. 4. **Consider state requirements too** - Don't forget that you may also need state wage statements depending on where your LLC was based. The good news is that this situation is more common than you'd think, and the IRS has established procedures to handle it. Just make sure all your numbers are accurate and you have documentation showing your good faith efforts to obtain the proper W-2.

Important note that I learned the hard way: How you CLAIMED the depreciation matters, not just how you COULD HAVE claimed it. If you took accelerated depreciation under MACRS or Section 179 expensing, the recapture rules still apply to what you actually deducted. In your example, even tho your selling at a loss overall, make sure your keeping good records of exactly what depreciation method you used and how much you claimed each year.

I went through something very similar with machinery I sold last year. Your calculation is spot on - since you're selling below your adjusted basis of $13,300 ($26,500 - $13,200), you have an ordinary business loss of $6,500 that you can deduct. No depreciation recapture applies here. One thing to watch out for though - make sure you have proper documentation of the original purchase price and all depreciation claimed. The IRS may want to see Form 4797 for the sale of business property, and you'll need to show the depreciation schedule. Also, if this equipment was claimed under Section 179 expensing in addition to regular depreciation, the loss calculation works the same way but the paperwork gets a bit more complex. The key thing to remember is that recapture only kicks in when there's actually a gain above your adjusted basis. In loss situations like yours, you're essentially getting an ordinary deduction that can offset other business income, which is actually more favorable than a capital loss would be.

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.