Thank you for mentioning this. I honestly hadn't even thought about the medical deduction angle. Between his cancer treatments and my surgeries, we easily spent over $15,000 out of pocket even with insurance. Do things like hospital cafeteria meals and parking at medical facilities count too? I had so many appointments and hospital stays.

Yes, many of those related expenses do count! Transportation costs to and from medical treatments (including parking fees at hospitals and medical facilities) are deductible. While regular meals generally aren't deductible, if you had to stay overnight for medical care, some meal costs might qualify. Also track any home modifications made for medical reasons, medical equipment purchases, and even mileage driven to pharmacies and doctor appointments. The IRS allows 22 cents per mile for medical travel in 2024. Many people miss these "secondary" medical expenses that can really add up over a year of intensive treatment.

That won't help in this case. OP specifically mentioned they don't have any children/dependents, so they wouldn't qualify for the Qualifying Widow(er) status in future years.

Do you think $200/month is worth it at my current size? That seems like a lot when we're only making about $6-7k in revenue (not profit). Did you find that the tax savings offset the bookkeeping costs right away or did it take time?

At your current size, you might look for a more limited arrangement. Instead of full monthly service, you could find someone who does quarterly reviews of your books for less money. I started with quarterly help at about $300 per quarter when my revenue was similar to yours. The value became apparent after the first tax season when she found several deductions I'd missed, like a portion of my home utilities for my home office and some vehicle expenses for deliveries. She also properly categorized some equipment that I could depreciate. The tax savings definitely outweighed the costs, even in the first year. As your business grows, especially in wholesale with inventory tracking, having properly maintained books becomes increasingly valuable.

Yes! This is so important. I'm in NY and got hit with some surprises too. OP, what state are you in? Some states treat pass-through entities very differently than others. Also, does your city have any special business taxes? Local taxes caught me completely off guard.

I'm in Texas, so no state income tax, but we do have franchise tax if the revenue gets above a certain threshold. Thankfully I've already got sales tax permits and exemption certificates for our cafe customers. Good reminder though - there are definitely a lot of moving pieces to keep track of!

I didn't have any other income, just this part-time job. What's the Earned Income Credit? Could I really get money back even though I barely paid anything in? That sounds too good to be true.

The Earned Income Tax Credit (EITC) is designed specifically for lower to moderate income workers. For tax year 2024 (filing in 2025), if you're single with no children and earned around $11k, you might qualify for a small credit - potentially a few hundred dollars. It's a refundable credit, which means you can get it even if you owe no taxes. There are age requirements though - you generally need to be at least 25 and under 65 to claim it without qualifying children. You'll need to file Form 1040 and complete Schedule EIC to claim it. Most tax software will automatically check if you qualify when you enter your information, so it's worth filing even if you don't owe any taxes!

Same thing happened to me in college. If you check "Exempt" you need to fill out a new W-4 every year or they automatically start withholding at the highest rate after February 15. Learned that the hard way lol.

What if I did a direct rollover from my 401k to Roth IRA without going through a traditional IRA first? My 1099-R has code G in box 7 but still has the full amount as taxable. Do I still need Form 8606 in this case?

If you did a direct rollover from a 401k to a Roth IRA, the process is a bit different. Code G indicates a direct rollover, but whether it's taxable depends on whether the 401k portion was pre-tax or after-tax money. If it was after-tax contributions from your 401k going directly to a Roth IRA, then yes, you would still want to override the taxable amount. However, Form 8606 is primarily for tracking basis in IRAs, not 401ks. You'll need to document your after-tax contributions to the 401k separately, usually by providing records from your plan administrator showing which portion was after-tax.

I e-filed with this exact scenario last year and had no issues. As long as you complete Form 8606 correctly, the e-file should go through fine. The IRS systems are built to handle this situation because it's actually pretty common with Roth conversions.

9 This is actually really bad advice. Filing an amended return to add income you intentionally left off initially could potentially trigger audit flags. The IRS might wonder what other income you "forgot" to report the first time. Better to just do it right the first time.

3 I think you're right about the potential audit concerns - I didn't consider that. My suggestion was more focused on privacy than tax optimization. A better approach would be what others have suggested - taking control of your own tax filing this year. Tax software makes it pretty straightforward, and it's an important adult skill to develop anyway.

1 I appreciate the suggestion but I'm nervous about even mentioning a medical company. My parents are pretty nosy and would definitely ask a ton of follow-up questions that I'm not prepared to answer convincingly. I think I'm going to go with filing my own taxes this year. It seems like the cleanest solution based on all the advice here. Thanks everyone for the help!