Your friend is partially correct but missing important details. You can deduct a portion of your car insurance - but only the percentage that corresponds to your business use of the vehicle. For example, if you use your car 60% for Doordash and 40% for personal use, you can deduct 60% of your insurance costs. However, if you're taking the standard mileage deduction (65.5 cents per mile in 2023), insurance is already included in that rate, so you can't deduct it separately. You'd need to be using the actual expenses method instead. Most dashers find the standard mileage deduction gives them a better tax benefit overall, especially if you drive a lot of miles.

Yes! Those are 100% legitimate business expenses that you can deduct. Insulated bags, space blankets, drink carriers, phone mounts for your car, portion of your phone bill used for dashing, portable phone chargers - all deductible as business expenses. Make sure you keep the receipts though! The IRS loves documentation if you ever get questioned. I actually take photos of all my receipts and store them in a dedicated cloud folder just to be safe.

My friend is a tax preparer and she says most W2 employees with straightforward situations are wasting money on professional preparation. Wouldn't someone be better off just using that money to increase their 401k contributions?

For truly straightforward W2 situations, your friend is probably right. If someone makes $60k with no dependents, minimal investments, and takes the standard deduction, professional preparation might not provide enough value. But the original poster is describing a much more complex situation - $580k household income, variable commission-based pay, and a new dependent. At that income level, even small optimizations can save significant amounts. The tax code becomes more complex at higher income levels, with various phase-outs, alternative minimum tax considerations, and planning opportunities. The value of proper tax planning typically far exceeds the cost of preparation in these scenarios.

Honestly, for your income level ($580k), I'd avoid H&R Block. Nothing against them, but they're generally better for straightforward tax situations. Most of their preparers don't have the specialized knowledge to optimize taxes for high-income professionals with variable compensation. You'd be better off with a CPA who specializes in working with sales professionals or high-income individuals.

Wait, I've been overseas for 8 months now. Does that mean I might have qualified for that automatic extension? Do they just give it to you, or do you need to specifically request it? Also, do you know if that Foreign Earned Income thing requires you to have been overseas for a certain amount of time?

The automatic 2-month extension is given automatically to US citizens living abroad - you don't need to request it. However, it only extends the original April deadline to June, not the October extension deadline. So in your current situation, it wouldn't help unfortunately. For the Foreign Earned Income Exclusion, you typically need to meet either the Physical Presence Test (physically present in foreign countries for at least 330 days in a 12-month period) or the Bona Fide Residence Test (establish residence in a foreign country for an uninterrupted period that includes an entire tax year). Since you've been abroad 8 months, you might qualify under the Physical Presence Test depending on your specific dates. It's definitely worth looking into because it could exclude up to $120,000 of foreign earned income from US taxation.

I've sent tax docs from Japan twice now. Definitely use a courier service like DHL or FedEx rather than regular mail. They're much more reliable and give you tracking info. The IRS address you use depends on whether you're enclosing a payment - it should be listed on the IRS website under "where to file." Make sure to keep copies of EVERYTHING and proof of mailing.

Thanks for this insight! The situation was definitely giving me red flags. I've requested my wage transcripts online as you suggested. Is there anything else I should be gathering to protect myself? I still have all my pay stubs and my copies of the W-2s they gave me each year.

Definitely keep all those pay stubs and W-2 copies in a safe place - they're your evidence that you were paid and taxes were withheld. Take photographs or scans of everything as backups. Also request your Account Transcript from the IRS, not just the Wage and Income Transcript. The Account Transcript will show if any taxes were credited to your account from withholding. If your pay stubs show withholding but your transcript doesn't show those payments, that's clear evidence your employer withheld but didn't remit the taxes.

Is filing that form anonymous? I'd be concerned about blowback from reporting a former employer, especially if they're already doing shady stuff.

Is there any way to verify directly with the IRS that your 1099s were properly filed? Or do you just have to trust the service you used?

Unfortunately, the IRS doesn't have a simple verification system for confirming 1099-NEC filings. This is why getting the acknowledgment receipt with submission ID from your e-filing provider is so crucial. You can call the IRS Business & Specialty Tax Line (800-829-4933) and ask them to check if your forms were received, but be prepared for long wait times and potentially inconclusive answers. Sometimes they can confirm receipt, but they often tell you to just wait to see if you receive any non-filing notices, which isn't very helpful when you're trying to be proactive.

That's incorrect information that could cause serious problems. The threshold change to 250 (not 25) forms was actually implemented years ago, then reduced back to 10 forms for 1099-NEC specifically. For the 2024 tax year (filing in 2025), the threshold is still 10 forms, meaning OP must e-file since they have 12 forms. Filing incorrectly based on misunderstood future rule changes could result in penalties. The safest approach is to follow current requirements and use an authorized e-file provider as suggested earlier.