I switched from a CPA ($550/year) to doing my own taxes with software 4 years ago and haven't looked back. My situation is similar to yours - W-2 income, investments, and a rental property. The first year took me about 5 hours because I was learning, but now I can finish in about 2 hours. The software walks you through everything, and there are tons of forums online where you can ask questions about specific situations. The big advantage is that I actually understand my tax situation better now. My CPA never explained why he was making certain choices, but now I know exactly where my money is going and how different decisions affect my tax liability. I did have my old CPA review my self-prepared return the first year (paid him for an hour of time), and he only found a minor issue that wouldn't have triggered an audit anyway.

Honestly, if you have a rental property AND a side business, I would NOT recommend doing your own taxes. I tried to save money last year and did my own with TurboTax. Ended up missing some key deductions and had to file an amended return that my friend (who's a CPA) caught. Cost me more in the long run. Maybe try negotiating with your current CPA? Or find a less expensive one? But with rental depreciation and business expenses, there's just too many places to mess up if you don't know what you're doing.

Just want to add something no one's mentioned - if you're using your personal vehicle for business driving, make sure your auto insurance knows you're doing delivery/rideshare! Many policies don't cover commercial use, and if you get in an accident while delivering, they might deny your claim. Most gig companies offer some coverage, but it's usually limited. I learned this the hard way after a small fender bender during a DoorDash delivery. My regular insurance wouldn't pay because I was "using the vehicle for commercial purposes" and DoorDash only covered liability, not my car repairs. Had to switch to a policy that specifically allows delivery driving.

You should also consider tracking your cell phone usage for business! Since you're using delivery apps, part of your phone bill can be deducted. Same with any accessories like phone mounts, chargers, or hotspot data you use while working. I usually deduct about 60% of my phone costs since that's roughly how much I use it for gig work.

Virginia resident here! Just wanted to add that updating your name with Virginia DMV and tax department can be done separately from your federal tax filing. You'll need to update your name with Social Security first, then DMV, then everything else. For Virginia state taxes, you'll file under whatever name is on your federal return for consistency. The Virginia tax department actually recommends filing under your old name if that's what your W-2 and Social Security records still show, even if you have a court order.

Honestly the worst part of changing your name is updating EVERYTHING. I changed mine last year and taxes were the least of my worries lol. Had to update my bank, credit cards, mortgage, car title, insurance, utilities, email addresses, subscriptions, professional licenses... the list goes on forever 😩 The key with taxes is definitely making sure your W-2 name matches your Social Security card name. Otherwise it'll get flagged in the system.

Just to add something I learned the hard way - even if you're a resident alien for tax purposes under the substantial presence test, make sure you check if you qualify for the "closer connection exception" if you genuinely plan to return to your home country after your studies/work. I declared myself as a resident alien and filed that way, then found out I could have maintained nonresident status (which would have been more beneficial in my case due to scholarship taxation differences). Had to file an amended return which was a huge hassle. Also, don't forget that state residency rules can be different from federal! My state doesn't follow the substantial presence test and has its own criteria.

Make sure you understand exactly what "exempt" means in the ADP system! There are different kinds of exemptions and selecting wrong can get you in trouble. "Exempt from withholding" means you expect NO federal income tax liability for the entire year (very rare). "Exempt due to tax treaty" is for specific nonresident alien benefits. If you're truly a resident alien now, you usually shouldn't be selecting either exemption option - you should just fill out the W-4 with your appropriate filing status, adjustments, deductions, etc.

Just to add another perspective - I've been doing my own taxes for 15 years using various software options. Last year I finally hired an EA because I started a small business and was terrified of making mistakes. Cost me $375 for both federal and state, which seemed high until I realized all the deductions she found that I would have missed. She literally saved me over $2,100 in taxes! What surprised me most was how much I learned during the process. She explained everything and gave me tips for better record-keeping this year. Software can ask questions, but it can't look at your specific situation and proactively suggest strategies like a human can.

Does anyone know if most CPAs or EAs offer some kind of free initial consultation? I'm not sure if I need help or not and don't want to pay just to find out.