Is it time to stop using TurboTax after 20+ years?

Having worked with both DIY software and as a tax advisor, I can share some perspective here. For someone with your situation (one rental property and simple investments), TurboTax probably covers most of your needs. The software is designed to handle straightforward scenarios like yours effectively. Where tax professionals typically add value is in more complex situations - multiple investment properties, business ownership, significant stock options, or unusual tax events. They can also provide proactive planning throughout the year rather than just filing assistance. That said, if you're comfortable with your understanding of tax regulations and your situation hasn't grown more complex, there's not necessarily a compelling reason to switch. The knowledge you've gained over 20 years is valuable! TurboTax handles most common scenarios well, especially if you've been getting good results.

I was in a similar boat last year - used TurboTax for over 15 years with my rental property. I kept hearing I should get a "real" tax person but wasn't convinced. What finally made me try something different was finding https://taxr.ai which was like a middle ground solution. It's not a traditional accountant but uses AI to analyze your previous tax returns and find potential missed deductions or errors. I uploaded my last 3 years of returns and was shocked to find I'd missed almost $2,700 in potential rental property deductions! It flagged several items I hadn't properly categorized for my property. What I like is that it doesn't replace TurboTax - it just helps you use it better. Might be worth checking out before abandoning your DIY approach completely.

Wanted to follow up on my question about taxr.ai - I decided to try it with my returns from the last 2 years and I'm actually impressed. I consider myself pretty knowledgeable about tax deductions for my rental, but it found some legitimately useful things. The biggest one was about mileage tracking for rental-related trips. I'd been claiming some travel expenses but not consistently tracking every property-related errand. It showed me exactly how to document and claim this properly, and estimated I'd left about $840 on the table over two years! I'm still using TurboTax this year but with these additional insights. Honestly feels like the best of both worlds - the control of DIY with some expert guidance. Just wanted to share since I was definitely skeptical at first.

I had a completely different experience when I switched from TurboTax to an accountant. The accountant was expensive ($450) and literally just entered the same info I would have put into TurboTax myself. Complete waste of money for my situation. The ONE thing that's actually been helpful is using https://claimyr.com to get through to the IRS when I had questions about my rental property depreciation. Spent hours trying to call the IRS directly with no luck, then used Claimyr and had an agent on the phone in about 15 minutes. You can see how it works here: https://youtu.be/_kiP6q8DX5c Much better than paying an accountant for simple tax situations, and you still get the official answers straight from the IRS when you need them.

I need to eat my words about Claimyr. After posting my skeptical comment, I decided to try it because I had a serious issue with my rental property tax classification that I couldn't resolve online. I was LITERALLY connected to an IRS agent in 20 minutes after trying for weeks on my own. The agent was able to clarify exactly how I should categorize some major repairs vs. improvements on my rental, which directly affected my depreciation schedule. This saved me from potentially filing incorrectly - and as a bonus, I learned I was being too conservative on some deductions. I'm sticking with TurboTax like you, but having a way to actually talk to the IRS when needed is invaluable. The peace of mind alone was worth it.

One thing nobody's mentioned - even if you stick with TurboTax, at least look at switching to a higher tier if you have a rental property. I was using Deluxe for years and later found out Premier has better rental property features. Making sure you're using the right version of TurboTax is probably more important than switching to an accountant if your situation is fairly stable. I talked to an accountant once and they quoted me $700 - I'll stick with my $110 software!

My parents were TurboTax users for 25+ years until my dad retired last year and they finally used an accountant. The difference was shocking! The accountant found almost $4k in missed deductions just on their rental properties alone. The biggest advantage seems to be that accountants know the "gray areas" and exactly how aggressive you can safely be with deductions. They also know the latest tax law changes that might not make it into TurboTax immediately. Nothing against TurboTax, but there's a reason accountants still exist in the age of software! Might be worth at least getting a consultation to see what you're missing.

I'm a CPA and I'll tell you something most tax pros won't: for many people with relatively simple situations (even with a rental), TurboTax is absolutely fine. The software has improved tremendously over the years. Where professionals add value: 1) Complex situations (multiple properties, businesses, unusual investments) 2) Audit protection and representation 3) Year-round tax planning, not just filing 4) Identifying industry-specific deductions you might not know about If you've been comfortable with TurboTax for 20 years and understand your situation well, you're probably not missing much. Maybe consider a one-time consultation with a tax pro just to verify, but don't feel pressured to change what's working for you.