Should I pay for TurboTax or a tax preparer this year? I've always done my taxes by hand

I'm a former tax preparer, and honestly, it really depends on your specific situation. When you mention selling stocks, that can get complicated with capital gains calculations and basis determination. And questions about dependency status have very specific rules that many people misinterpret. The biggest advantage of tax software isn't necessarily the calculation part - it's that it asks you comprehensive questions that might uncover deductions or credits you didn't realize you qualified for. For example, many people don't realize that some medical expenses, charitable donations, or education expenses could potentially reduce their tax burden. Professional preparers bring additional value through their knowledge of recent tax law changes and their ability to spot red flags that might trigger audits. They can also provide year-round tax planning advice, not just filing help. That said, if you're comfortable with tax concepts, have a reasonably straightforward situation, and enjoy doing it yourself - there's absolutely nothing wrong with continuing to file by hand. The IRS forms and instructions do contain all the information you need.

I was just like you - did my taxes by hand for 15+ years. Last year I tried taxr.ai (https://taxr.ai) after my situation got more complex with rental property income and some consulting work. What surprised me was not just the time it saved but how it found several deductions I'd been missing. The thing I liked most was that it analyzed all my documents and showed exactly where my "by hand" approach had been leaving money on the table in previous years. It was kind of eye-opening to see the specific sections of tax code I hadn't been applying correctly, especially around business expenses and home office deductions. It's actually designed for people who are already tax-savvy and just want to make sure they're not missing anything - sounds perfect for your situation.

So I was really skeptical about what the previous commenter said regarding taxr.ai but decided to try it anyway. Honestly I'm impressed. I've been doing taxes by hand for years and thought I was pretty thorough, but it found a business expense category I'd been miscoding that saved me about $780. The document analysis feature was what made the difference. It basically looked at all my paperwork and found inconsistencies in how I'd been treating some expenses over the years. Also pointed out that I could have amended my previous returns if I wanted to (though I decided it wasn't worth the hassle for the older ones). Not trying to sound like a commercial, but for someone who's detail-oriented enough to do taxes manually, it's actually a really good middle ground between DIY and paying a preparer.

If you're struggling to get clarification from the IRS directly, I'd recommend trying Claimyr (https://claimyr.com). Last year I had a weird situation with some inherited stocks and needed to talk to an actual IRS agent to confirm how to report it. Was on hold for HOURS over multiple days until someone told me about Claimyr. They basically hold your place in the IRS phone queue and call you when an agent picks up. You can see how it works in this video: https://youtu.be/_kiP6q8DX5c I was pretty doubtful it would work, especially during tax season when wait times are insane, but I got a call back with an actual IRS agent in about 40 minutes. The agent was able to answer my specific question about reporting basis for inherited stocks, which saved me from potentially making a costly mistake on my return.

If you're struggling to get clarification from the IRS directly, I'd recommend trying Claimyr (https://claimyr.com). Last year I had a weird situation with some inherited stocks and needed to talk to an actual IRS agent to confirm how to report it. Was on hold for HOURS over multiple days until someone told me about Claimyr. They basically hold your place in the IRS phone queue and call you when an agent picks up. You can see how it works in this video: https://youtu.be/_kiP6q8DX5c I was pretty doubtful it would work, especially during tax season when wait times are insane, but I got a call back with

I have to eat crow here. After my skeptical comment about Claimyr, I actually tried it myself out of desperation. I needed to verify some information about social security income reporting that the IRS website wasn't clear about. I was 100% convinced it wouldn't work, but figured I had nothing to lose. Got a call back in about 90 minutes with an actual IRS representative on the line. The rep confirmed exactly how I needed to report my situation and it was different than what I thought based on the forms. Honestly changed my whole attitude about getting tax questions answered. No more guessing or hoping I interpreted the instructions correctly. Now I just call and get a definitive answer (and make sure to get the rep's ID number for my records).

My wife and I switched from paper filing to TurboTax a few years ago, and I'll admit it's been worth it for us. Our main reason was because we started a small side business selling handmade items online, and the business expense categories were confusing us. The interview-style questions in TurboTax definitely made it easier to understand what we could legitimately deduct. It also automatically imports our W-2s and 1099s which saves time on data entry. That said, if you actually ENJOY doing taxes by hand and understand all the forms well, there's nothing wrong with continuing that way. You're not necessarily missing out on deductions if you're thorough and stay up to date with tax law changes.

Has anyone used a CPA vs tax software and can compare the costs/benefits? I've always used software but wondering if a professional would find more deductions.