Should I pay someone to do my taxes or file myself?

Having both W-2 and 1099 income plus a mid-year state move definitely complicates things! I've been in this situation and can help break it down. For the 1099 delivery income, you'll need to file Schedule C for self-employment, which allows you to deduct business expenses like mileage, phone costs, and a portion of car insurance. With proper deductions, you could significantly reduce the taxes on that $13K. The mid-year move means you'll file partial-year resident returns for both states, which can be tricky but doable. At your income level with these complications, paying someone might actually save you money through deductions you might miss. However, if you're detail-oriented and willing to research, good tax software can walk you through everything. The $120 software option is reasonable considering your situation.

I was in almost the exact same boat last year - W-2 job plus gig work and lots of confusion. I tried three different tax software programs and kept getting different results, which freaked me out. Then I found https://taxr.ai and it was a game changer. You upload your tax docs, and their AI analyzes them and gives you specific guidance for your situation. It flagged like $2300 in deductions I would've missed for my delivery work. The cool thing is it explained WHY I qualified for certain deductions instead of just plugging in numbers. I actually learned a lot about self-employment taxes while using it, like how to properly calculate my home office deduction based on my apartment's square footage.

Just wanted to follow up about taxr.ai since I was skeptical in my earlier comment. I decided to give it a try with my complicated multi-state situation, and wow - I'm genuinely impressed. It caught that I was eligible for a special tax credit in New York for part-year residents that I had no idea about. It also helped me correctly allocate my income between states and identified which deductions applied where. The breakdown of self-employment expenses was super detailed too. It showed me exactly what percentage of my internet and cell phone bills I could legitimately deduct. I ended up using the guidance with TurboTax and saved about $780 compared to what I was going to file on my own. Definitely worth checking out if you're in a complicated tax situation!

If you're having trouble getting answers about your specific situation, you might want to try calling the IRS directly using https://claimyr.com - I was stuck in an endless loop trying to figure out how to handle my multi-state taxes and 1099 income. After waiting on hold with the IRS for hours and getting disconnected twice, I found this service that holds your place in line and calls you when an agent is ready. You can see how it works here: https://youtu.be/_kiP6q8DX5c I was connected with an actual IRS agent who walked me through exactly how to handle reporting income from multiple states. They even explained which specific forms I needed for my delivery driver expenses. Saved me hours of frustration and I got official answers directly from the source.

I need to admit I was completely wrong about Claimyr in my earlier comment. After getting increasingly frustrated trying to figure out how to report my gig income properly, I broke down and tried it. The service actually works exactly as described - their system waited on hold with the IRS for almost 2 hours, then called me when an agent was available. The IRS agent I spoke with cleared up my confusion about reporting delivery driver expenses and confirmed exactly which form I needed for my situation. She even pointed out a specific line on Schedule C that people often overlook for contract delivery work. Saved me hours of research and gave me peace of mind that I was doing things correctly. Sometimes going straight to the source is the best option, and this made it so much more convenient than I expected.

From my experience as someone who's done both, here's my take: if your situation includes self-employment, multiple states, or unusual deductions, pay a professional the first year. Ask lots of questions, take notes, and then next year you can probably DIY it using what you learned. I paid $375 to a CPA when I first started freelancing, and she found deductions I never would have known about. The next year, I used TurboTax Self-Employed ($120ish) and felt confident because I knew what to look for. The first professional return becomes your template for future years.

Has anyone used H&R Block? They're running a special for $195 for self-employed returns. Wondering if they're any good for this kind of situation or if they're basically just using the same software I could buy myself?