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.

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.

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.

Does this apply to utilities too? I kept utilities on in my name for about 2 months after moving out while finding a tenant. Can I deduct those as rental expenses or does the "available for rent" rule mean I'm out of luck?

For utilities specifically, you can deduct them as rental expenses once the property is "available for rent" - meaning it's being marketed as a rental, even if you don't have a tenant yet. The key is having documentation that shows you were actively trying to rent it out (listing photos, advertisements, etc.). If you kept utilities on simply while deciding what to do with the property or while making repairs before putting it on the market, those expenses aren't deductible yet. It's all about when you officially changed the property's purpose to "income-producing.

I used TurboTax for a similar situation last year. In my experience, it does a slightly better job with rental property partial year usage. There's a specific screen that asks about dates of conversion and it has separate entries for expenses during the rental period vs. the whole year.

Where would you find this "key" if your company doesn't have an employee handbook? My small business employer just hands us checks with random deduction codes and gets annoyed when we ask questions.

Legally, your employer is required to provide clear information about your pay and deductions. If they don't have an employee handbook, they should still provide this information when you're hired or upon request. For small businesses without formal HR departments, sometimes the payroll codes come from whatever payroll software they're using. You could try asking specifically for the "payroll deduction code sheet" or "earnings and deductions key." If they continue to refuse, you can contact your state's labor department, as this could potentially violate wage transparency laws in many states.

Yes! My company switched payroll providers mid-year and suddenly all the codes changed even though the actual deductions stayed the same. What was MED became HLTH and 401K became RETIR. No explanation provided - it's like they want us to be confused about our own money.