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!

I hadn't thought about checking for residual distributions. That's a great point! Do you know if the broker would have sent any notification about this, or would I need to call them specifically to ask?

They typically send a notification, but these can easily get missed, especially if they went to an old email address or got filtered as spam. I'd definitely recommend calling your broker directly and asking if there were any final distributions related to the company. Sometimes these distributions are very small (like pennies per share) but they still affect your tax basis. Also, ask if they have any record of the exact date the shares became worthless in their system. Brokers often have this information officially recorded, which can be very helpful for tax documentation.

This is a really important point. I've seen people miscalculate their basis on ESPP shares all the time. The Form 3922 should show the FMV and the actual purchase price, right? So you can figure out what the discount was?

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!