Make sure you keep ALL your receipts and get itemized billing. I had a similar situation with a jaw surgery that was partially covered. The oral surgeon wrote a letter explaining the medical necessity of correcting my bite for TMJ but acknowledged the cosmetic improvement too. I was able to deduct about 70% of the total cost. Also remember you need to itemize deductions to claim this, so if you take the standard deduction it won't help you.

Don't forget timing matters too! For the 2025 tax year, you can only deduct medical expenses that exceed 7.5% of your adjusted gross income. So if your AGI is $80,000, you'd need more than $6,000 in medical expenses before you could start deducting anything. And you'd need enough other itemized deductions to exceed the standard deduction ($13,850 for single filers in 2024, probably higher for 2025).

Something else to consider - if you're still incorporating the charity, these might be startup costs rather than regular business expenses. The IRS allows you to deduct up to $5,000 in startup costs in your first year of business, with the rest amortized over 15 years. But the meal would still be subject to the 50% limitation within that startup cost category.

Great question! I went through something very similar when starting my nonprofit last year. Here's what I learned from my accountant and through experience: You absolutely need to keep that itemized receipt - not just the credit card slip. Write on the back (or keep separate notes) the name of the vendor, their company, and a brief summary of what business topics you discussed related to your charity. The IRS wants to see clear business purpose, so something like "Discussed website development services for [charity name] - reviewed pricing and timeline for donor portal" works well. Since you're still incorporating, I'd recommend creating a simple spreadsheet to track these pre-launch expenses separately. They'll likely be classified as startup costs rather than regular business expenses, which has different deduction rules (up to $5,000 first year, rest amortized over 15 years). One tip: don't stress about taking formal notes during the meal - that would be awkward! Just jot down the key business points discussed within a day or two while it's fresh. The goal is showing the IRS this was a legitimate business meeting, not a social lunch. Remember the 50% deduction limit applies even for nonprofits, and keep the expense "reasonable" - fancy steakhouses might raise eyebrows, but normal business lunch spots are fine. Good luck with your charity launch!

FYI - your former employer is breaking the law. Employers are required to provide W2s by January 31st, and they must respond to requests for replacement W2s in a reasonable timeframe. You can actually file a complaint with your state's labor department as well as with the IRS.

I'm dealing with a similar situation right now and honestly, your former employer is being completely unprofessional. From what I've learned through my own research, you have several solid options that don't require your ex-boss to cooperate. The IRS wage transcript route is definitely your best bet for speed - you can get it online immediately through irs.gov if you create an account. This will have all the same info as your W2 and is completely legitimate documentation that state tax departments regularly accept. You should also absolutely report your former employer to the IRS at 800-829-1040. They're legally required to provide your W2 and the IRS takes this seriously. Even if it doesn't help you immediately, it might prevent them from doing this to other former employees. One thing I'd add is to document everything - save those texts where you asked for the W2, keep records of your calls to ADP, etc. This creates a paper trail showing you made good faith efforts to get your W2, which strengthens your case if there are any questions from tax authorities later.

15 Does anyone know if Form 8936 requires any additional documentation to be submitted with your return? I'm also claiming the EV credit this year and heard different things from different preparers.

Just to add another perspective here - I'm a tax preparer and that $390 fee from H&R Block is definitely inflated for your situation. While the 1098-T and Form 8936 do add some complexity, many preparers would charge closer to $200-250 for that combination. The EV credit is actually pretty straightforward once you understand the basics - you need the vehicle's VIN, purchase date, manufacturer, and model year. The software handles most of the calculations automatically. The education credit from the 1098-T is even more routine. If you're comfortable with technology at all, I'd strongly recommend trying the online route first. You can always start with free software to see how far you get, and if you run into issues, then consider paying for professional help. But honestly, your situation sounds very manageable for DIY filing.

Has anyone used a corrective distribution to fix excess employer contributions in a solo 401k? My understanding is you need to file Form 1099-R with a specific code to show you're correcting an excess. But I'm not sure if this applies to employer side contributions or just employee.

I'm dealing with a similar excess contribution situation right now. One thing I learned from my tax advisor is that you should also check if your excess contribution might qualify for the "deemed distribution" rule under IRC Section 415. If your total contributions (employee + employer) exceeded the annual limits, sometimes the IRS allows you to treat the excess employer contribution as a taxable distribution rather than subject to the 6% excise tax. This doesn't make it deductible, but it might be a better outcome than paying the excise tax annually. Also, make sure you're calculating your maximum employer contribution correctly for next year. As a self-employed person, your employer contribution limit is based on your net self-employment income minus half of your self-employment tax, not your gross 1099 income. A lot of people trip up on this calculation.