22 Do credit card fees really add up to that much though? And even if they do, isn't it illegal to deduct those from reported contractor payments? I thought the 1099 was supposed to show the gross amount paid.

5 Credit card fees typically run 2-3%, so no, they wouldn't account for a $4,800 discrepancy unless your brother earned well over $150,000 from this one shop. You're absolutely right that the 1099-NEC should show the gross amount paid to the contractor before any fees. What sometimes happens (incorrectly) is that salon owners might deduct booth rental fees or product charges before calculating the 1099 amount. This is incorrect - those should be handled separately, and the 1099 should reflect the total payments made to the contractor.

1 Thank you all for the advice! I'm showing my brother this thread tonight. He does keep pretty good records with a booking app that tracks all his appointments and payments, plus he has his bank statements showing deposits. I think we'll start with a formal written request for a corrected 1099-NEC, and if that doesn't work, he'll report the full income anyway and keep all his documentation ready. And maybe check out some of these services you've all recommended to make sure he's handling everything correctly!

Thanks for that warning. My goal isn't to change careers - I'm planning to expand my real estate portfolio and possibly move into commercial properties in the future. Would that still count as my "current" business or would the IRS see commercial real estate as a new trade?

Expanding from residential to commercial real estate would generally still be considered the same trade or business since you're still in property management and real estate investment. The IRS would likely view this as a natural progression within your current business rather than entering a new field entirely. Going from real estate into something completely different like investment banking (as in my case) is what triggers the "new trade or business" limitation. Just make sure you document your intention to expand within real estate rather than presenting it as preparation for a career change.

In TurboTax, you'd enter it under the Schedule E section for your rental property. When you get to the expenses part for each property, there's an "Other Expenses" category where you can add custom expense items. That's where I put my real estate continuing education costs last year.

Wait, can employers actually do that? I assumed once the year was over, all the tax stuff was set in stone. Can they really go back and fix withholding errors after the fact?

They can't change the actual withholding after the year ends, but there are a couple of options. First, they can issue a corrected W-2 if there were actual errors in reporting. More practically though, some employers will provide compensation to cover tax liabilities resulting from their payroll errors - basically paying you an additional amount to offset some of your tax burden. This isn't required by law, but many companies have policies for this since payroll errors can cause significant financial hardship for employees. It's worth having a conversation with both HR and payroll about their error resolution policies. Document everything, be polite but firm that this was their error, and ask what they can do to help make it right.

Exactly this! The IRS calls it a "Waiver of Penalty Due to Federally Declared Disaster, Mathematical or Clerical Error by the IRS, or Certain Other Conditions" (Part II of Form 2210). A payroll system error could qualify under certain conditions!

Does this also work with retirement account withholding? I take distributions from my IRA and could potentially increase the withholding there instead of making estimated payments.

Yes, it absolutely works with retirement account withholding too! Any federal income tax withholding (from W-2 wages, retirement distributions, etc.) is treated as if it occurred evenly throughout the year, regardless of when it actually happened. So increasing your IRA distribution withholding late in the year is a perfectly valid strategy to make up for estimated payment shortfalls. It's especially useful if you realize in November or December that you're going to owe more than expected.

Thank you for clarifying this! I was looking at the wrong line on my previous return. Looks like I need to pay about $2,400 more than I thought to hit the safe harbor. Better to know now than get hit with penalties later!

Wait really? The mileage deduction is that much? I never tracked my miles but I was doing Doordash like 4 nights a week for about 8 months. How would I even calculate that now after so much time has passed?

You can create a reasonable estimate based on your delivery history. Most delivery apps keep a record of your deliveries - try to get that data from Doordash if you can. If that's not possible, make a good faith estimate. Calculate your average deliveries per shift, estimate miles per delivery (including driving to pickup locations), and multiply by your working days. Document how you arrived at this estimate in case of questions. For 4 nights a week for 8 months, you're looking at roughly 128 working days. Even at a conservative 30 miles per shift, that's 3,840 miles or about $2,150 in deductions! Just be honest but thorough - this could significantly reduce what you owe.

Good point about state taxes. One thing to add - some cities also have local income taxes that apply to self-employment income. I found out the hard way after getting a notice from my city tax department a year after dealing with the IRS!