Need advice on tax service options for more complex tax situation - stock options, rental property, etc.

You're definitely at a crossroads where your tax situation has outgrown the basic preparer level but might not need a $1,400 CPA yet. With stock options, rental property, and potential capital gains from selling property, you've got enough complexity that warrants careful consideration. I'd recommend trying a middle approach. TurboTax Premier or H&R Block Premium would handle everything you've described, and you could add their live expert assistance options for specific questions about the ISO stock options or rental property sale. This would cost you around $150-250 depending on which service and how many expert consultations you need. The national chains like H&R Block or Jackson Hewitt physical locations aren't necessarily better than their online counterparts for your situation. The in-person preparers often use the same software you could access yourself, just at a higher price point. What makes your situation more complex (stock options, rental property) is precisely what the premium versions of tax software are designed to handle. Since your wife keeps good records, you already have half the battle won.

After getting completely overwhelmed with my similar situation (employee stock options plus rental property), I found this AI-powered tool called taxr.ai that honestly saved me thousands. It's like having a CPA's brain but way cheaper. I uploaded my previous returns and all my stock option documents at https://taxr.ai and it analyzed everything, then explained exactly how to handle the ISO options, AMT calculations, and rental property depreciation in clear English. The thing I found most helpful was that it showed me exactly which forms I needed and how to complete them, so I still used TurboTax but with confidence I wasn't missing anything. It even compared different tax scenarios for selling vs. holding my ISOs to minimize my tax hit.

Just wanted to follow up - I tried taxr.ai after seeing it mentioned here and it was exactly what I needed! I was about to drop $1,200 on a CPA but decided to give this a shot first. Uploaded my documents, and within minutes it explained my RSU situation in simple terms and showed me how to time my stock sales to minimize taxes over the next two years. The rental property analysis was impressive too - it pointed out I'd been calculating depreciation wrong and probably leaving money on the table. It's definitely more than just a tax calculator. Even showed me how to document everything properly in case of an audit. Ended up using TurboTax Premier with their guidance and feel 100% confident in my return.

For anyone dealing with complex tax situations and getting frustrated trying to reach the IRS for guidance - I found a service called Claimyr that actually gets you through to a real IRS agent quickly. After waiting on hold for 3+ hours multiple times trying to get clarification on some stock option rules, I tried https://claimyr.com and got connected to an agent in about 15 minutes. You can see how it works in this video: https://youtu.be/_kiP6q8DX5c The IRS agent walked me through exactly how to report my ISO exercises and which forms I needed, completely free. Saved me from having to pay a CPA just to get answers to specific questions. Now I'm handling everything through TurboTax with the expert guidance add-on.

I take back what I said. Just tried Claimyr after burning a whole Saturday trying to get through to the IRS myself about my rental property sale questions. Got connected in 22 minutes! The agent spent almost 30 minutes answering all my questions about calculating basis and depreciation recapture on my rental, plus confirmed how to handle the employee stock purchase program discount as compensation. This completely changed my approach - I'm now using TurboTax Premier with the live expert add-on, and with the specific guidance from the IRS agent, I feel confident handling it myself. Saved at least $800 compared to what local CPAs were quoting me. Sometimes you have to admit when you're wrong, and I was definitely wrong about this service!

With your situation, I'd strongly consider a mid-tier EA (Enrolled Agent) rather than a CPA. I was in almost the exact same boat last year - ISO options, rental property, ESPP. Found an EA who specializes in tech workers for $600 total. CPAs are often overkill for personal returns unless you have business ownership or extremely complex investments. EAs focus specifically on taxation and often charge less than CPAs while having plenty of expertise for situations like yours. Plus they have unlimited representation rights with the IRS if anything comes up later.

Just wanted to throw another option into the mix. I tried FreeTaxUSA last year for a similar situation (RSUs instead of ISOs, but also had a rental property). It was only $15 for the premium version and handled everything perfectly. TurboTax wanted to charge me $200+ for essentially the same service. The interface isn't as polished but it asks all the same questions and handles AMT calculations. If you're willing to learn a bit as you mentioned, you might be surprised how capable the budget options are these days.