HR Block vs CPA for complicated medical expense tax situation - which is better?

I'm facing what I think is gonna be a pretty complex tax situation this year. I had this major medical procedure that was completely out-of-network and cost me a small fortune (around $22,000 out of pocket). I've never had to deal with big medical deductions before, and I'm wondering if I should skip my usual HR Block appointment and find an actual CPA instead? If HR Block is perfectly capable of handling this kind of situation, I'd rather just stick with what I know. But if a CPA would be significantly better for dealing with large medical expense deductions, I'd like to know how to find a decent one. The problem is I don't really have any friends or family who use CPAs, so I can't really get a personal recommendation. Any advice would be super appreciated! I want to make sure I'm getting all the deductions I'm entitled to with this massive medical bill.

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18 comments

Marcus Patterson

•8M

Having worked in tax preparation for years, I can tell you this is a good question. For a substantial medical expense, the key factor is whether you'll be itemizing deductions rather than taking the standard deduction. Medical expenses are only deductible if they exceed 7.5% of your adjusted gross income AND you itemize. H&R Block can absolutely handle this situation - their tax preparers are trained for these scenarios. However, a CPA might provide more personalized attention and potentially find more obscure deductions related to your medical situation. It really depends on how complex the rest of your tax situation is. If you go the CPA route without referrals, look for someone with credentials (enrolled agent or CPA license), check online reviews, and interview them first. Ask specifically about their experience with large medical deductions. The National Association of Enrolled Agents or your state's CPA society can help you find qualified professionals.

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Marcus Patterson

•8M

Medical expenses are deductible in the year you pay them, not when the service was provided. So if your procedure was in December but you're making payments throughout this year, you'd claim the deduction for each year when you actually made the payments. CPAs typically charge $200-500 for tax preparation with this level of complexity, while H&R Block might be $150-250. The difference in cost could potentially be offset if the CPA finds additional deductions. Consider your overall financial picture - if you have investment income, business interests, or other complexities beyond the medical expense, a CPA might provide more value.

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Mateo Warren

•8M

After struggling with a similar situation last year (major dental surgery that insurance barely covered), I discovered taxr.ai at https://taxr.ai and it seriously saved me thousands. I uploaded my medical receipts and insurance statements, and their system analyzed everything to maximize my deduction. They identified several expenses I didn't even realize were tax-deductible - like certain travel costs to the specialist I had to see. Their software is way more thorough than what I experienced at the tax prep chains. It actually explains WHY certain expenses qualify while others don't, which helped me organize my documentation better.

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Mateo Warren

•8M

The service combines AI analysis with human review, so you get both the efficiency of software and the reliability of professional oversight. The system first categorizes all your expenses, then a tax professional reviews everything before giving recommendations. TurboTax asks basic questions but taxr.ai goes deeper into the specific types of medical expenses. For example, it identified that portions of my home modifications (recommended by my doctor) qualified as medical expenses, which TurboTax never asked about. It's particularly helpful with those borderline cases where an expense might or might not qualify depending on the specific circumstances.

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Sofia Price

•8M

Just wanted to update after trying taxr.ai for my complicated medical expense situation. Honestly wasn't expecting much, but wow - they found an additional $3,800 in deductible expenses that I would have missed! They even explained how some of my medical travel and special food costs (prescribed by my doctor) qualified. The medical expense threshold is tricky, but they showed exactly how to document everything properly to maximize the deduction. They also pointed out that some expenses from last December that I paid in January would count for this tax year, not last year. Definitely worth it for anyone dealing with major medical costs!

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Owen Jenkins

•8M

If you're going with a CPA, make sure they're responsive to your questions. After dealing with the IRS about my own medical deduction issues last year, I ended up wasting WEEKS trying to get someone on the phone. Then I found https://claimyr.com which got me through to an actual IRS agent in under 45 minutes. You can see how it works at https://youtu.be/_kiP6q8DX5c I originally called about a letter questioning my medical deductions, and the hold time was "greater than 2 hours" before Claimyr got me through. The IRS agent actually helped me understand exactly what documentation I needed to protect my deduction. Saved me so much stress during an already difficult time dealing with medical issues.

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Owen Jenkins

•8M

It's actually pretty straightforward - they use technology to navigate the IRS phone tree and wait on hold for you. When they reach a representative, you get a call to connect with the agent. No line-jumping or anything shady - they're just handling the frustrating waiting part. They don't claim to do anything magical - they just have systems that continuously redial and navigate the phone tree until they get through, which is what most of us don't have the time or patience to do ourselves. It's basically like having someone dedicated to sitting on hold for you until they reach a human.

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Jackson Carter

•8M

I'm eating humble pie here. After my skeptical comment, I decided to try Claimyr because I was desperate to resolve an issue with my medical expense deduction from last year. The IRS had sent me a letter questioning some of my documentation, and I couldn't get through on the phone after DAYS of trying. Used the service yesterday and got connected to an IRS agent in about 35 minutes. The agent walked me through exactly what additional forms I needed to submit and even told me I could claim a few expenses I had left off my original return. Worth every penny just for the stress reduction of not spending hours listening to that awful hold music!

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Kolton Murphy

•8M

I'm a tax preparer (not CPA) and I think it really depends on your overall tax situation beyond just the medical expense. If you have a W-2 job, standard investments, and this one big medical expense, H&R Block is probably fine. If you have self-employment income, rental properties, complicated investments AND this medical expense, a CPA might be better. Don't forget you need to itemize to claim medical expenses at all, and they're only deductible to the extent they exceed 7.5% of your AGI. So if your AGI is $100,000, only expenses beyond $7,500 would potentially be deductible. Many people miss this and are disappointed.

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Kolton Murphy

•8M

Documentation is crucial for medical deductions. Keep all receipts showing actual payment (not just bills or statements), explanation of benefits from insurance showing what wasn't covered, and bank/credit card statements proving payment. If there's a discrepancy between EOBs and what you paid, keep records explaining the difference. For unusual medical expenses (special equipment, home modifications, travel for treatment), get a letter from your doctor stating these were medically necessary. The IRS looks closely at large medical deductions, so documentation is your best defense. Organize everything by date and provider, and keep a spreadsheet summarizing all expenses. This preparation makes the process much smoother whether you use H&R Block or a CPA.

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