One thing to consider is that the raffle organizers might be overvaluing the car on the 1099-MISC. I've seen charities list the MSRP rather than actual market value. You have the right to challenge the amount on the 1099 if you have documentation showing the actual FMV is lower. Kelley Blue Book or other valuation services can help establish the real market value. If you can document that the car is actually worth less than $62,500, you could potentially report the lower amount on your taxes with an explanation.

I'd strongly recommend getting professional help with this situation since there are several moving parts that could significantly impact your tax liability. With a prize this large, even small mistakes in reporting could be costly. A few additional considerations beyond what others have mentioned: 1. **State taxes**: Don't forget about state income tax implications - depending on your state, this could add another 5-10% to your tax bill. 2. **Timing of sale**: If you're selling immediately, make sure you have proper documentation showing the sale price and date. This creates a clear paper trail if the IRS has questions. 3. **Professional valuation**: If there's a significant difference between the stated value and what you can actually sell for, consider getting a professional appraisal done before the sale. This could support your position if you need to dispute the 1099-MISC amount. 4. **Cash flow planning**: With potential taxes around $18,000-20,000 (federal + state), make sure you're setting aside enough from the sale proceeds. You don't want to be caught short at tax time. Given the complexity and the amounts involved, this might be worth paying for a consultation with a tax professional who has experience with prize winnings, even if your regular guy isn't available. The cost of advice could easily pay for itself in tax savings and peace of mind.

Thank you all for the helpful responses! I think I'm going to go with the de minimis approach since all my purchases are under $2,500 and it seems simpler than tracking depreciation. I'll definitely create that accounting policy document today. One final question though - if I buy something that costs more than $2,500 later this year, can I still depreciate that specific item even if I used de minimis for my other purchases? Or do I have to be consistent with one approach for all assets?

Great thread! Just wanted to add one more tip that helped me when I was starting out as self-employed - consider the timing of your purchases if you're expecting your income to vary significantly year to year. If you're in a lower tax bracket this year but expect higher income next year, immediate deductions (like de minimis) give you the tax benefit now when it might be worth less. But if you expect to be in a higher bracket in future years, depreciation spreads the deduction over time when it might be more valuable. For most new self-employed folks with the amounts you mentioned, de minimis is still probably the way to go for simplicity, but it's worth considering your income trajectory. Also, don't forget that if you're using part of your home as an office, you might be able to claim the home office deduction for that space too!

Has anyone used the corporate credit card approach? My accountant suggested getting a separate credit card for my S-Corp, putting all client-reimbursable expenses on that card, and then recording the reimbursements as direct payments against those specific expenses in my accounting software rather than as income.

This thread has been incredibly helpful! I'm in a similar situation as the original poster - just converted to S-Corp this year and have been struggling with how to handle client meal reimbursements properly. One thing I wanted to add that might help others: make sure you're keeping contemporaneous records of the business purpose for each meal. The IRS requires documentation of who you met with, what business was discussed, and the specific business relationship. Even with client reimbursement, you still need this documentation to support that it was a legitimate business expense in the first place. I learned this the hard way when my previous accountant told me I just needed receipts, but during a review, I realized I was missing the business purpose documentation for about half my meals. Had to go back through old calendars and emails to reconstruct what each meal was for. Now I write the business purpose right on the receipt when I get it, or immediately add it to my expense tracking app. Also, for anyone using the separate credit card approach that @Zoe mentioned - make sure that card is officially in your S-Corp's name, not just a personal card you designate for business use. The legal separation is important for maintaining your corporate protections.

Has anyone tried using the IRS standard mileage deduction? I heard that's 66.5 cents per mile for 2025 tax year. Would that apply in this situation?

This is such a common confusion in the events industry! I've been working as a tax preparer for 8 years and see this situation constantly with event staff, wedding vendors, and similar workers. The key thing to understand is that even though your workplace changes daily, the IRS still considers your travel from home to your first work location as "commuting" - which isn't deductible for W-2 employees under current tax law. However, there are a few potential bright spots in your situation: 1. **Travel between work sites**: If you work multiple events in the same day at different locations, the mileage between those locations IS potentially deductible business travel. 2. **Employer reimbursement**: This is honestly your best bet. Many event companies do reimburse travel when it's a regular job requirement. Document your mileage and approach them professionally. 3. **Classification review**: Sometimes event workers should actually be classified as independent contractors rather than employees, which would change your deduction eligibility entirely. I'd recommend keeping detailed mileage logs regardless - if your employment classification ever gets reviewed or if tax laws change, you'll want that documentation. And definitely push for employer reimbursement since these are legitimate business expenses from their perspective.

I legit gave up on TAS after 3 months of waiting. Their whole system is a joke rn honestly

I feel your pain @Rami - been there myself. One thing that helped me was calling the TAS intake line directly at 1-877-777-4778 about 2 weeks after submitting Form 911 to check status. Sometimes they can give you a case number or at least confirm they received it. Also make sure you have all your documentation ready because when they do call, they'll want everything immediately. Hang in there!