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.

Would it be better to fax the response instead of mailing it? I've heard the IRS processing centers have huge backlogs of mail but faxes get entered into their system faster.

In my experience, faxing can be faster but only if you have confirmation the fax went through successfully. The IRS fax lines are often busy or don't connect properly. I'd recommend doing both if possible - send via certified mail for your records and also try faxing. The key thing regardless of method is making your documents super clear and organized. Put your notice number, SSN (last 4 digits only for security), and tax year on every single page. The IRS processes millions of pieces of correspondence and making yours easy to identify with the right case helps tremendously.

That doesn't sound right. If someone incorrectly claimed you as a dependent when you weren't actually qualified to be one, you should still be eligible for your own stimulus payment. The IRS even has procedures for resolving these exact situations.

That's helpful, thank you. How much should I expect to pay for a quality preparer who will do both (ensure accuracy and find legitimate deductions)? I don't want to overpay, but I also understand that expertise costs money.

For a situation like yours with a home purchase and some freelance work, expect to pay somewhere between $350-600 for a quality tax preparer, depending on your location and the complexity of your freelance activities. If your freelance work is more involved with lots of expenses and equipment, it might go higher. It's an investment, but a good preparer can often find deductions that more than cover their fee. Just make sure whoever you choose is asking detailed questions about your situation rather than just collecting your W-2s and basic info. The more questions they ask, the more likely they're looking for those legitimate deductions you might qualify for.

What kind of deductions triggered your audit? I'm always nervous about claiming home office or business expenses even though I legitimately work from home half the time.

That's a really good point I hadn't considered. We're not planning to sell anytime soon, but the housing market in our area has been growing pretty rapidly. Do you know if there are any requirements about how long you need to be married to qualify for the full $500k exclusion when selling?

To qualify for the full $500K married exclusion when selling, you need to have owned and lived in the home as your primary residence for at least 2 of the last 5 years before selling. And you need to be married when you sell the house, not necessarily when you bought it. The ownership test and the residence test are separate, so you need to meet both. As long as you're married when you sell and meet those requirements, you should be eligible for the full $500K exclusion regardless of when the marriage occurred during your ownership period.

This is such a good point. My husband and I both owned properties before marriage in high-tax states and got absolutely crushed by this after getting married. We literally pay thousands more in taxes now because of the SALT cap. If you're in a high-tax state, run the numbers carefully.

Thanks for mentioning this! I think I might actually have some suspended passive losses from years when my income was too high to claim them. How exactly do I check for this? Is it on a specific form from previous tax returns?

You'd need to look at your Form 8582 (Passive Activity Loss Limitations) from previous tax years. If you had passive losses that couldn't be used in a particular year due to income limitations, they would be carried forward and should be documented there. The unused losses accumulate over the years, and when you dispose of the property in a taxable transaction (like your sale), you can generally use all the suspended losses related to that property. This could significantly reduce the tax impact of your sale and the depreciation recapture.

Cost segregation is great when you're starting out with a property because you can accelerate depreciation on components with shorter lives (5, 7, 15 years instead of 27.5 years for residential). But it's a double-edged sword when selling because you'll face recapture on those components too. The benefit is that personal property components (5-7 year property) get recaptured at your ordinary income rate, not the 25% rate that applies to real property depreciation. So if your tax bracket is lower than 25%, it can help.