This happened to me! I had filed an extension and when I finally did my taxes, I got rejected because I had typed my SSN wrong on the extension form. Had to call the IRS to sort it out. Super annoying.

Oh man, that's scary. I haven't noticed anything unusual with my credit or accounts, but now I'm worried. How would I check if someone filed a fraudulent return with my info?

This is super helpful! How do I figure out how much to pay each quarter though? My income isn't consistent at all - some months I make a lot more than others depending on projects.

You have a couple of options. The safest approach is to estimate your annual income and divide your expected tax liability by four. But since your income fluctuates, you can also use the "annualized income" method (Form 2210, Schedule AI), which lets you make payments based on what you've actually earned by each quarterly due date. A simpler approach many freelancers use is to set aside 25-30% of each payment you receive, then use that money for your quarterly payments. This usually covers both income tax and self-employment tax for most people. Adjust the percentage if you find you're consistently over or underpaying.

I used TurboTax Self-Employed last year for my design business and it worked pretty well. It walks you through all the deductions and explains what qualifies. The only tricky part was figuring out the home office deduction but they have a calculator for that too. Definitely cheaper than an accountant if your situation isn't super complicated.

Thanks for this list! I hadn't thought about the phone mount or dashcam. Can you really deduct Spotify though? I use it while driving but isn't that kind of a gray area?

You can deduct Spotify if you're using it specifically for your business - like providing music for passengers as part of your service. It's considered a business expense if it's primarily for your customers' experience. If you're just listening to it yourself while doing DoorDash deliveries, that would be much harder to justify as a business expense since there are no passengers benefiting from it. It's all about whether it's necessary for your business operations versus personal enjoyment.

Yup, this is super important! I made that mistake with my first delivery car. I used actual expenses the first year when the car was new and had higher value for depreciation. When the car got older and needed fewer repairs, standard mileage would have been better but I was stuck with actual expenses. For parking and tolls - gig drivers should use apps that track these separately! I use the Stride app for mileage and the Everlance app to snap photos of parking receipts. Makes tax time way easier.

Thanks for pointing this out! I didn't realize that choosing actual expenses would lock me in for the life of the vehicle. That's definitely something to consider since I might keep this car for several years. And I had no idea about the parking fees and tolls! I've probably spent around $200 on parking in downtown areas for pickups/deliveries. Good to know I can deduct those on top of the standard mileage.

Does this apply to supplemental property tax bills too? I thought those were different since they're retroactively assessing tax for periods before the bill was created.

Supplemental property tax bills are actually a good example of properly assessed taxes. Since the supplemental bill has already been issued with specific amounts and due dates, it has been officially assessed by the tax authority. The concern I was mentioning applies more to trying to prepay future regular property tax installments that haven't been billed yet. With supplemental bills, both installments are typically assessed at the same time when the bill is issued, even though the second payment is due months later. So paying both installments in the same tax year for deduction purposes is usually fine with supplemental bills.

Yes! We challenged our supplemental bill and got it reduced by about $1,800. The key is to file the appeal quickly - most counties have a deadline of 60 days after receiving the bill. We provided our closing documents showing the actual purchase price and they adjusted it.

I've heard this "replacement cost" approach too, but what about when you're wearing multiple hats? In my small S-Corp, I'm the CEO, marketing department, sales, and janitor. Should I be calculating different reasonable salaries for each role?

That's a great question and something I struggled with too! My accountant advised documenting the approximate percentage of time spent in each role, then calculating a blended "replacement cost." For example, if you spend 30% of time on high-level strategy (CEO work), 50% on billable service work, and 20% on admin tasks, you'd calculate what each of those roles would cost to replace, multiply by the percentage of time, and add them up. This approach acknowledges that not all your time is spent on the highest-value tasks, which helps justify a lower overall salary while still being "reasonable.

The minimum wage approach can work as a starting point, but it depends on your specific situation. For highly skilled professions (doctors, lawyers, consultants, etc.), the IRS would likely challenge minimum wage as "reasonable" since the market rate for those services is much higher. However, for businesses with tight margins in less specialized fields, documenting your hours and paying at least minimum wage could be defensible - especially if you clearly document your business circumstances and why this approach makes sense for your situation. The key is having that documentation ready if questioned.