I tried the import feature but it only pulled in half my transactions for some reason. Did you run into any issues with missing transactions? And did TurboTax detect all your wash sales correctly?

I did actually have that happen on my first attempt! The problem was that my PDF had two pages, and TurboTax only imported the first page. I had to combine all the Stash PDF pages into a single document and then it worked perfectly. As for the wash sales, yes - TurboTax identified them correctly after importing. I double-checked a few transactions manually and everything matched up with what was on my 1099-B. Just make sure when you're reviewing that the "Box A" checkbox is marked for covered securities, since that's what most Stash investments are.

I noticed the same thing! Stash rounds to the nearest cent on tiny fractional purchases, which creates these small discrepancies. If the difference is just a few cents, I wouldn't worry about it. The IRS isn't going to come after you for pennies. But if you're seeing bigger discrepancies, definitely worth investigating.

Thanks for confirming I'm not going crazy! The discrepancies are mostly small - under a dollar for each transaction. I was just worried because there are so many tiny transactions that it might add up. Good to know this is normal with fractional shares and rounding. I'll stop obsessing over the pennies!

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!

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 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!

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!