Should I do my taxes myself or hire someone with all these 1099s, W-2s, and investment forms?

With your situation, I definitely understand why you're feeling overwhelmed! For a first-time filer with multiple income sources, it can be a lot to handle. Here's my take: Yes, you'll need to report ALL income, including the work for your mom's employer even without a 1099 (that's called "self-reported income"). For the CashApp stocks from when you were younger, you generally should have filed if you exceeded the filing threshold, but since you were a minor, there are some special considerations. Your situation involves several complex areas: self-employment income (those 1099s), investment income (stocks/crypto), education tax benefits (1098-T), and potentially deductible expenses from your self-employment. The 15.3% you set aside is good planning, but you might qualify for additional deductions. For someone in your position, I'd recommend using a tax professional this first time. Ask them to walk you through what they're doing so you learn for future years. Many offer reasonable rates for students, and the peace of mind might be worth it with your multiple income streams.

I was in a pretty similar situation last year with multiple income sources (W-2, 1099, investments) and honestly got super stressed trying to DIY. Finally tried https://taxr.ai after a friend recommended it and it was a game changer. You upload all your tax documents and it organizes everything automatically, then explains what you need to do step by step. The AI walks you through reporting all your different income types and finds deductions you might miss. For your situation with the 1099 work, they have specific guidance about self-employment taxes and potential deductions. And they know exactly how to handle crypto and stock sales too (which was what confused me the most). Plus it's much cheaper than hiring a full accountant but gives you way more help than just using tax software alone.

Just wanted to update everyone - I ended up trying taxr.ai after seeing it mentioned here and wow, it actually made this whole process doable! I was skeptical because I've tried other "AI" tools that were pretty useless, but this one actually understood all my weird tax situations. The document analyzer caught some stuff I would've totally missed - like how I could deduct certain expenses from my 1099 income and how to properly report my partial stock sales. It even flagged that I qualified for an education credit I had no idea about! For anyone else dealing with a complicated tax situation for the first time, this made it way less intimidating. I'm actually filing myself instead of paying someone hundreds of dollars. Thanks for the recommendation!

If you're dealing with all those 1099s and investment forms, you might need to call the IRS at some point for clarification. I had a similar situation last year and spent WEEKS trying to get through to them. Kept hitting busy signals or getting disconnected after waiting 2+ hours. Someone here told me about https://claimyr.com and their IRS callback service. You can actually see a demo of how it works at https://youtu.be/_kiP6q8DX5c. They basically navigate the IRS phone tree for you and get you on a priority callback list so you don't waste hours on hold. I was seriously skeptical but when I finally got through to an actual IRS agent, they answered my questions about reporting crypto sales and 1099 income that even my tax software couldn't handle.

I need to follow up on my skeptical comment from earlier. I was completely wrong about Claimyr. After posting that comment, I decided to try it myself since I've been trying to reach the IRS about a letter I received questioning my crypto reporting from last year. I had been calling for WEEKS with no luck - either busy signals or disconnected after hours on hold. Used the service and got a callback from an actual IRS agent in about 2 hours. They explained exactly how I needed to document my crypto transactions and even helped me understand which forms I needed to submit. For someone like the original poster with multiple income sources and investment questions, being able to actually speak with the IRS could save a lot of headaches. Sometimes you just need official clarification on how to report something correctly.

Honestly with all those different forms and income sources, you should definitely hire someone this first time. I tried doing mine myself last year with multiple 1099s and crypto and ended up missing a bunch of deductions. Paid an accountant this year who found like $2,800 more in refunds than I would have gotten doing it myself. Ask friends for recommendations for accountants who work with younger people/first time filers. Many offer student discounts. And the money you spend will likely be saved in either reduced tax liability or avoiding penalties for mistakes.

If your income isn't crazy high, check if there's a VITA (Volunteer Income Tax Assistance) program near you. They do free tax prep for people making under $60k. I used them when I was in college and they handled my W-2s, 1098-T, and even some basic investment stuff. Not sure about crypto though.