Thanks for the direct answer! I'll definitely get that resale certificate squared away first. For the charitable contribution part - if I explicitly note on the invoice that I'm offering a 5% charitable discount to the nonprofit, can I then claim that 5% as a charitable contribution? Or does it have to be a completely separate transaction?

You can document the discount as a charitable contribution on the same transaction, but you need to explicitly state it as a "charitable discount" or "donation" on the invoice. Keep in mind you're not donating the item - you're donating a portion of its value through the discount. The important thing is clear documentation. Your invoice should show the regular price, then the charitable discount amount as a separate line item (not just a generic "discount"), and note the nonprofit's tax ID number. This creates the paper trail you need. And remember, this has nothing to do with sales tax - it's completely separate.

Direct pay permits saved my sanity! I run a supply company and dealing with all the different exemption certificates was a nightmare. Now about 80% of my tax-exempt customers use direct pay and I don't have to worry about their documentation. Definitely worth asking your customers about.

Thanks for bringing up disability insurance - that's something I definitely need to address. Do you have suggestions on what percentage of income should be covered? And regarding the student loans vs. retirement accounts, would you recommend maxing out all available retirement vehicles before accelerating loan payments?

For disability insurance, most financial advisors recommend covering 60-70% of your income, but as a surgeon, you should look for specialty-specific coverage with true "own-occupation" definition of disability. This means you get paid if you can't perform surgery specifically, even if you could still work in medicine in other capacities. Regarding retirement vs. loans, it depends on the interest rates, but generally yes - max out tax-advantaged accounts first, especially if your loans are under 6-7%. The tax advantages of retirement accounts (particularly when combined with the right business structure) almost always outperform the guaranteed return of paying off low or moderate interest debt. With your income level, you should be able to make significant progress on both simultaneously.

Completely agree. I use Gusto for my S-Corp payroll and it's been seamless. Automatically handles all the tax filings, makes the correct deposits, and generates all the required forms. The reasonable compensation question for S-Corps is where having a good CPA really helps though.

Did you have to pay self-employment taxes on the 1099 income? I'm in a similar situation and wondering if that approach would cost more than just reporting it as regular income.

Yes, I did have to pay self-employment taxes, which was about 15% on top of regular income tax. That was definitely the downside of the 1099 approach. But what helped offset some of that was being able to deduct legitimate business expenses that I wouldn't have been able to deduct otherwise. I was able to write off a portion of my phone bill (since I was on call), work boots, tools I purchased, and even mileage when I had to drive to purchase supplies. My tax guy helped me identify all the eligible deductions, which reduced the taxable income substantially.

This is actually a really good point. I think OP needs to clarify whether they were hired with the requirement to live there, or if they were a tenant first and the work arrangement came later. That seems to be the crucial factor.

Thanks for suggesting this form! I've never heard of being able to request a mid-year refund directly from the IRS. Do you know roughly how long the processing time is if I submit Form 8379? I'm weighing whether to wait for my July paycheck as they suggested or try to speed things up with this form.

The processing time varies, but generally it takes 6-8 weeks after they receive the form. That might not be faster than waiting for your July paycheck if that's coming in the next few weeks. Actually, I need to correct something - I meant Form 843 (Claim for Refund and Request for Abatement), not Form 8379. Form 8379 is for injured spouse relief, which is something completely different. My mistake on the form number!

IRS2Go doesn't let you request withholding adjustments - it just lets you check refund status, make payments, and access tax records. For withholding issues you still need to work through your employer or call the IRS directly.

Not a dumb question at all! You're right that the Tax Cuts and Jobs Act suspended the deduction for unreimbursed employee expenses for tax years 2025-2025. Your brother might be deducting his dues in one of these ways: 1. He's self-employed and deducting them on Schedule C 2. His employer reimburses him through an accountable plan 3. He lives in a state that still allows these deductions on the state return (like California or New York) 4. He's in a specialized profession that still qualifies (certain performing artists, state/local government officials, armed forces reservists, or fee-basis government officials) Or, unfortunately, he might be taking a deduction he's not entitled to, which could cause problems if he's audited.