Heads up - you might also want to check if your current car insurance covers delivery driving. Most standard policies don't, and if you get in an accident while delivering, they might deny your claim. I found out the hard way unfortunately.

Great question! I was in a similar situation last year - working part-time and picked up DoorDash to make ends meet. Here's what I learned: You're right to be thinking about taxes early! Since DoorDash classifies you as an independent contractor (not an employee), you won't get a W-4 from them. Instead, you'll receive a 1099-NEC if you earn $600+ in a year. For your primary job's W-4, I'd recommend updating it to account for the extra income. A good rule of thumb is to set aside about 25-30% of your DoorDash earnings for taxes (this covers both income tax and self-employment tax). You can have your main employer withhold extra from each paycheck by putting an additional amount in line 4(c) of your W-4. Also, start tracking your mileage from day one! It's your biggest potential deduction. I use a mileage tracking app and it saved me hundreds last tax season. One more tip - if you think you'll make more than $1,000 from DoorDash this year, you might need to make quarterly estimated tax payments to avoid penalties. The IRS has worksheets to help calculate this. Good luck with the side gig! It definitely helped me get through some tight months.

Anyone have experience with H&R Block's handling of Form 2210? TurboTax always seems to calculate a penalty for me even when I don't think I should have one, wondering if switching software would help.

I had this exact same issue! The key thing to understand is that Line 8 on Form 2210 should be the SMALLER of two amounts, not necessarily your full 2023 tax liability. Since you mentioned having 110% of your 2023 tax withheld, you should definitely qualify for safe harbor protection. The problem might be that TurboTax isn't correctly applying the "deemed paid evenly" rule for W-2 withholding. Here's what worked for me: I manually calculated Form 2210 using both the regular method and the annualized income installment method to see which gave me a lower penalty (or no penalty). Sometimes the software defaults to one method when the other would be more favorable. Also, double-check that TurboTax is correctly pulling your 2023 tax amount. I've seen cases where the software uses the wrong line from the prior year return, especially if you had refundable credits that affected your actual tax liability vs. what you owed. If you're still getting a penalty calculation after verifying these details, you might want to file Form 2210 manually with your return to override the software's calculation.

24 Has anyone compared whether it's better to claim ABA therapy under the medical expense deduction instead of the dependent care credit? I heard you can't double-dip and claim the same expenses for both.

Great question about comparing the medical expense deduction vs dependent care credit! I actually ran into this exact dilemma last year with my daughter's speech therapy costs. Here's what I learned: The dependent care credit is usually better because it's a direct credit (reduces taxes owed dollar-for-dollar) vs a deduction (only reduces taxable income). Plus, medical expenses only help if you itemize AND they exceed 7.5% of your AGI. For example, if you're in the 22% tax bracket and claim $3,000 in medical deductions, you save about $660 in taxes. But if you use that same $3,000 for the dependent care credit at 20%, you save $600 directly off your tax bill - and potentially more if you qualify for a higher credit percentage based on income. However, if you already have massive medical bills that put you over the 7.5% threshold anyway, then adding the therapy to medical might make sense. I'd recommend calculating both scenarios to see which gives you better overall tax savings!

Has anyone dealt with selling investments in your home country after becoming a US tax resident? I'll be moving on H1B soon and have some stocks I'm wondering if I should sell before or after I become a US tax resident.

Great question! I went through this exact same process two years ago when I moved from India on H1B. Let me break down what I learned: You'll likely be a "nonresident alien" for your first partial year (2025 if you arrive next month), then become a "resident alien" in 2026 once you pass the Substantial Presence Test. The key thing to remember is that your H1B status doesn't automatically make you a tax resident - it's all about days physically present in the US. For your first year filing, you'll need Form 1040NR (nonresident alien return). This is actually simpler in some ways because you only report US-source income. You won't need to report your foreign accounts immediately unless they generate US-source income. One thing that caught me off guard: make sure your employer withholding is correct for your status. Many payroll systems default to resident withholding, which can cause issues. I had to work with HR to adjust my W-4 for nonresident status in my first year. Also, keep detailed records of your entry/exit dates from the US - you'll need these to calculate your days for the Substantial Presence Test. I use a simple spreadsheet to track this. The transition from nonresident to resident filing can be tricky, so definitely consider getting professional help for at least your first couple years. The forms and rules are quite different between the two statuses.

I went through something very similar last year! Missed a $42 1099-INT from a CD that matured. I was panicking about whether to amend or not. Here's what I learned: the IRS matching system is pretty good at catching these, but for small amounts like yours, the consequences are really minimal. I ended up getting a CP2000 notice about 8 months later. The additional tax was only $9, plus about $1.50 in interest. No penalties at all. The notice was actually very straightforward - it showed exactly what was missing and gave me options to either agree and pay online, or dispute if I thought they were wrong. I just paid it through the IRS website and never heard from them again. For $31, you're looking at maybe $5-8 in additional tax depending on your bracket. Honestly, the stress of amending might not be worth it. Most people in your situation just wait for the notice and pay the small amount when it comes. Just keep that Bank of America 1099-INT handy in case you need to reference it later. Don't lose sleep over this - it's way more common than you think!

As someone who's dealt with this exact scenario, I can tell you that $31 is really nothing to lose sleep over. The IRS processes millions of returns and their automated systems are designed to catch these discrepancies, but for such small amounts, the consequences are minimal. Here's my take: you have two realistic options. You could file an amended return (1040-X) to be completely proper about it, which would cost you time but give you peace of mind. Or you can wait to see if the IRS sends you a CP2000 notice, which they probably will in 6-12 months. If you get the notice, you'll owe the additional tax (likely $5-8 based on your income level) plus minimal interest. The IRS rarely applies penalties for small, honest mistakes like this, especially on amounts under $50. Given that you're already stressed about it and you mentioned not wanting to pay to amend for such a small amount, I'd personally just set aside $15-20 in a savings account and wait for the notice. When it comes, you can pay it online in about 5 minutes and be done with it. The key thing is that this won't trigger an audit or any major consequences. It's just a simple math correction that happens to thousands of taxpayers every year.