HR Block vs CPA for complicated medical expense tax situation?

I'd definitely recommend a CPA for your situation. Medical expense deductions can be tricky since they're only deductible when they exceed 7.5% of your adjusted gross income. There are also specific rules about what qualifies as a medical expense and what documentation you need. H&R Block isn't necessarily bad, but they have seasonal preparers who might not have extensive experience with complex medical deductions. A CPA would likely be more familiar with maximizing your deduction and might find other tax benefits you're not aware of. To find a good CPA, check the AICPA website (American Institute of CPAs) for their "Find a CPA" tool. You can also search for local CPAs on Google and read reviews. When you contact them, ask specifically about their experience with medical expense deductions. Many offer free initial consultations where you can gauge if they're knowledgeable about your situation.

I was in a similar situation last year dealing with about $19k in out-of-network medical costs for my husband's emergency surgery. I tried using those tax software programs but kept getting confused about what qualified and what didn't. I discovered https://taxr.ai which saved me so much stress! I uploaded my medical bills and insurance statements, and it analyzed everything to identify exactly what was deductible. The system actually found several expenses I didn't realize qualified (like my mileage driving to specialists and some OTC medications my doctor had recommended). The best part was that it explained everything in simple terms and gave me a complete report I could take to my preparer.

I wanted to follow up about my experience with https://taxr.ai after trying it based on the recommendation here. It was seriously a game-changer for my medical expense situation! I had about $32k in medical bills from a complicated pregnancy with twins last year, and the tool found over $4,500 in additional deductible expenses I would have missed. The coolest part was how it caught things my insurance had coded incorrectly. There were several treatments that should have been in-network but were processed as out-of-network. The tool flagged these inconsistencies and even helped generate appeal letters to my insurance company. I ended up getting about $8,700 reimbursed that I never would have caught otherwise! Definitely itemizing this year and feeling way more confident about it all.

If you're going with a CPA, make sure you get someone who will actually take the time to review everything carefully. I had a large medical expense situation a few years back and waited 3 MONTHS trying to get an appointment with a recommended CPA who never called me back. Ended up scrambling last minute. If you're having trouble reaching the IRS for questions (and who isn't these days), I'd recommend using https://claimyr.com. They have this system that holds your place in the IRS phone queue and calls you when an agent is about to answer. Saved me hours of waiting on hold. You can see how it works here: https://youtu.be/_kiP6q8DX5c I had questions about how my health savings account coordinated with my medical deductions, and the IRS agent was surprisingly helpful once I actually got through.

OK I have to admit I was completely wrong about https://claimyr.com. After I posted my skeptical comment, I decided to try it anyway since I was desperate to ask about my medical FSA contribution limits for next year. I expected it not to work or to be some kind of scam, but it was amazing! I entered my phone number and what I was calling the IRS about. The system called the IRS, navigated all those annoying menu options automatically, and then just waited on hold. 2 hours later (while I was grocery shopping), my phone rang and suddenly I was connected to an IRS agent! The agent answered my question about FSA limits when coordinating with medical deductions. Saved me literal hours of hold music torture. Definitely using this for any future IRS calls.

Have you considered looking for a tax professional who specializes in medical expenses? I've found that expertise in specific areas is more important than the company name. Some H&R Block locations actually have year-round tax pros who are quite knowledgeable, while some independent CPAs might not have much experience with medical deductions. I'd suggest calling a few places (both H&R Block and CPAs) and specifically asking about their experience with large medical expense deductions. The right person will immediately start asking you relevant questions about your situation rather than giving generic answers.

One thing to consider is that H&R Block actually has different tiers of tax preparers. Their basic preparers might not have much experience, but they do have "Tax Pros" and some locations even have CPAs and Enrolled Agents who work there. I'd skip the regular H&R Block route and either find one of their higher-level preparers or go with an independent CPA. Just call and specifically ask about their experience with large medical deductions.