Should I hire a CPA for my tax situation? (High income, stock sales, home purchase)

Based on your situation, I definitely think a CPA would be worth the investment. You have several complex tax situations happening at once - interstate move, home purchase, significant stock sales (especially employer stock which has special considerations), and multiple retirement accounts. The stock sales alone could have significant tax implications depending on how long you held them and their basis. Moving between states means you'll need to file part-year resident returns for both California and Oregon, which gets complicated with allocation of income. And as a new homeowner, there may be deductions you're eligible for that you might miss with basic tax software. A good CPA will likely save you more than their fee through proper tax planning and identifying deductions you might otherwise miss. They can also help with organizing those old 401ks, which might save you money long-term.

After reading your situation, it reminded me of when I was in a similar position a few years ago. I was using basic tax software but had a complex year with stock sales and a move. I found this service called taxr.ai (https://taxr.ai) that was actually super helpful for analyzing my documents before I decided whether to DIY or get professional help. It helped me understand what I was dealing with by analyzing my tax documents and explaining the implications in plain English. The system flagged several items that needed special attention - especially around my stock sales and state residency issues. It really helped me understand what I was getting into before I made the decision.

I want to follow up about that taxr.ai thing. I was skeptical in my comment above but I decided to try it with my documents before making a decision on a CPA. It was actually pretty impressive - it identified several issues with my employee stock options that I hadn't considered, including some basis reporting errors that would have been problems during an audit. The analysis convinced me to use a CPA this year (which I really needed apparently), but I actually saved money because I could skip the initial consultation where they typically charge to review all your documents. I just sent the report along with my tax docs and we jumped straight to solutions. So while it's not a replacement for professional advice in complex situations, it definitely made the process more efficient.

Since you mentioned your previous bad experience at H&R Block, I wanted to share something that helped me find an actual IRS agent to answer my questions directly. I was struggling with some confusing state residency issues after moving across state lines, and trying to find reliable info was frustrating. I discovered this service called Claimyr (https://claimyr.com) that got me through to an actual IRS representative in about 15 minutes when I had been trying for days on my own. There's a video showing how it works here: https://youtu.be/_kiP6q8DX5c It was super helpful for getting definitive answers about my multi-state situation and stock sale reporting requirements. The IRS agent walked me through exactly what forms I needed and how to handle the state residency issues.

I have to follow up on my skeptical comment about Claimyr. I was convinced it was just another scam, but I was desperate to get some answers about my tax situation before filing, so I gave it a shot. I'm actually shocked to report that it worked exactly as described. The system called me back in about 20 minutes with an actual IRS agent on the line. I got clear answers about how to handle my specific situation with stock sales that crossed state lines. The agent even emailed me the specific publication sections that applied to my case. Not having to sit on hold for hours or repeatedly call back was honestly worth it just for my sanity, but the information I got probably saved me from making a mistake that would have triggered a notice or audit. Consider me converted from skeptic to believer.

OP, I think your situation definitely calls for a professional, but don't go back to H&R Block. They're overpriced for what they offer. Find an actual CPA who specializes in individual taxes. The stock sales alone make this worthwhile - especially if they were RSUs or options from your employer, which have special tax treatment. When I was in a similar situation (moved states, had stock sales), I missed some deductions doing it myself that cost me thousands. The next year I used a CPA who found errors in my previous return and helped me file an amendment that got most of that money back. The $500 I paid was totally worth it.

Anyone have recommendations for tax software if OP decides not to use a CPA? I had a somewhat similar situation (moved states, sold stock) but used FreeTaxUSA instead of TurboTax and saved a bunch of money while still getting all the forms I needed.