Should I hire a CPA to do my taxes this year?

Do you think it's just worth it for this one complicated year, or should someone keep using a CPA once they start? Also, how much should I expect to pay for a decent CPA?

For many people, using a CPA for just the transitional year with major changes makes sense, then you could return to software once your situation stabilizes. If your side business continues growing, however, ongoing professional help often pays for itself through optimized deductions and tax planning. Regarding cost, it varies widely based on location and complexity, but for your situation, expect $250-500 for tax preparation. While that's more than software, a good CPA often saves you more than their fee through deductions you might otherwise miss and helping you avoid costly errors.

Does it actually work with complicated situations? I tried another tax tool last year and it couldn't handle my rental property situation at all.

I'm curious about the security - aren't you worried about uploading all your financial docs to some random website? How do you know it's safe?

It absolutely handles complicated situations - the AI is specifically designed for complex tax scenarios like rental properties, multi-state income, and business deductions. I had income from three different states last year and it handled everything perfectly. Regarding security, I had the same concern initially! They use bank-level encryption and don't store your actual documents after analysis. Plus they're SOC 2 compliant which means they've been independently verified for security standards. I researched them thoroughly before uploading anything.

Wait what? How does this even work? The IRS phone lines are notoriously impossible to get through. Is this legit or some kind of scam?

Yeah right... I'll believe it when I see it. There's no way to "skip" IRS hold times. Sounds like a waste of money to me.

It uses a combination of automated systems and priority routing to maintain your place in the queue. Instead of you sitting on hold, their system does it for you and calls you when an agent is about to be available. Nothing sketchy - they don't impersonate you or anything like that. The service exists because the IRS phone system is so dysfunctional. It's completely legitimate - they've been featured in major publications and have thousands of reviews from people who've used it successfully. Not a magic solution, just a smart workaround for a broken system.

How did you find your CPA? Did you just google or get a referral? I'm worried about ending up with someone who doesn't know what they're doing.

I got a referral from another small business owner friend - definitely the way to go if possible! Ask around to people in similar situations as yours. If that's not an option, check reviews but specifically look at responses from people with tax situations similar to yours. A good interview question is asking potential CPAs about their experience with your specific situation (side business, interstate move, etc). If they start immediately mentioning specific deductions or considerations for your situation without prompting, that's usually a good sign they know their stuff!

That's a really good point about the time aspect. I spent like 6 hours just trying to figure out how to categorize my side business expenses last year with the software, and that was before all these new complications. Maybe paying someone is worth it just for the stress reduction alone!