Wait - quarterly tax payments? Nobody told me about that! So I have to pay taxes four times a year now? How do I even know how much to pay when I don't know how much I'll make with DoorDash?

Yes, when you're self-employed the IRS wants you to pay taxes throughout the year, not just at tax time. It's because you don't have an employer withholding taxes from each paycheck. You estimate how much you'll make for the year and calculate your quarterly payments based on that. You can use last year's income as a basis, or if your income varies a lot, you can use the "annualized income installment method" which lets you pay based on what you've actually earned each quarter. If you use tax software, it will usually calculate your estimated payments for the next year and even generate payment vouchers.

Is it better to take the standard mileage deduction or track all your car expenses separately (gas, maintenance, etc)? I've been doing Doordash for 6 months and just writing down my miles.

Thanks for this advice! I'll ask my accountant about Form 911 tomorrow. Does filing this form have any downsides? Does it ever annoy the examiner or make them more likely to be thorough/harsh with the audit?

There are no downsides to filing Form 911. The Taxpayer Advocate Service exists specifically to help in situations like yours where normal procedures aren't working. Examiners understand this is part of the process and won't take it personally or be harsher as a result. In fact, in my experience, having TAS involvement often leads to more reasonable outcomes because it adds another layer of oversight to the audit process. The important thing is that you're demonstrating your willingness to cooperate and resolve the matter appropriately, which is always viewed favorably.

Try calling right when they open (7am Eastern I think). That's the only time I've had success. Also, don't select the option for "questions about a letter you received" because that queue is always full. Instead, choose "questions about tax law" and then just explain your situation once you get a human. They'll transfer you.

Thanks for the tip! I'll try calling at 7am tomorrow. It's crazy we have to use these workarounds just to talk to someone at the agency that's taking our money. Appreciate the suggestion about which option to select too - I've been picking the "letter" option since that matches my situation.

Mine took 32 days this year! Filed January 28th and didn't get my refund until March 1st. No special situations or anything complicated either, just a standard return with W-2 income only. I think they're just backed up.

That's crazy! Wonder if they're understaffed or something. Did you ever get an explanation for why it took so long? And did the status bar on the "Where's My Refund" tool update regularly or was it just stuck for weeks?

Filing an amended return shouldn't affect the processing of your original return - they're handled separately. Your original refund should proceed normally, and then the amended return (Form 1040-X) will be processed afterward. However, be prepared for a long wait on the amended return. Those typically take 16 weeks or longer to process, especially during peak tax season. Also worth noting that amended returns have to be processed manually, so they tend to take much longer than regular returns.

How can you tell which distributions are qualified vs non-qualified? My 1099-DIV has all these different boxes and I'm never sure what they mean.

On your 1099-DIV, qualified dividends will be in Box 1b, while Box 1a shows total ordinary dividends (which includes both qualified and non-qualified). The difference between Box 1a and 1b would be your non-qualified dividends. Capital gain distributions will be in Box 2a. These are the fund's long-term capital gains that get the preferential tax rate. If the fund had to distribute short-term capital gains, those would actually be included in Box 1a as ordinary dividends, not in the capital gains box, which is why it can get confusing!

I've used TurboTax for years with my mutual funds. It works OK if your brokerage provides good 1099s with detailed cost basis info. You can import directly from most major brokerages which helps avoid mistakes. But for older funds where you've been reinvesting for 10+ years, sometimes you need to manually adjust things, which can get complicated in TurboTax.

Does this change if it's a sole proprietorship though? Since the business income passes through to the business owner's personal return anyway? I'm confused about how this works since technically the money would be taxed on someone's personal return either way.

Great question about sole proprietorships. You're right that the income ultimately flows to someone's personal return, but it matters WHO reports it. The income should flow through the Schedule C of the actual business owner (father-in-law), not OP. Even though it's all "personal income" eventually, the proper reporting chain matters. If reported incorrectly as OP's income, they're being taxed on money they never received or controlled. Plus, the father-in-law's business isn't showing its true income, which creates problems for both parties. The key is getting the income attributed to the correct taxpayer, even if both are individuals in the eyes of the IRS.

The Taxpayer Advocate Service can be amazing but they're extremely backlogged right now. I applied for help in January and didn't hear back until April. They're prioritizing cases with immediate hardship (like impending house foreclosure or can't afford medications). Based on what OP described, they might qualify if the tax bill is causing severe financial hardship, but I'd pursue multiple paths simultaneously rather than waiting on TAS.