Is deducting medical expenses worth it for my situation?

Medical expense deductions can definitely be worth it in your situation, but it depends on a few factors. Since your medical expenses are around $8,000 and your income is $55,000, you're right that you exceed the 7.5% threshold (which would be about $4,125 for you). This means you could potentially deduct around $3,875 from your taxable income. The actual tax savings depends on your tax bracket. If you're in the 22% bracket, that could mean savings of roughly $850. If you're in the 12% bracket, it would be around $465. But remember, this only works if you itemize deductions instead of taking the standard deduction, which is $13,850 for single filers in 2025. Unless your total itemized deductions (including these medical expenses, plus things like mortgage interest, charitable giving, etc.) exceed the standard deduction, there's no benefit.

I was in a similar situation last year with about $9k in medical expenses across multiple providers. I tried gathering everything myself and it was a nightmare until I found taxr.ai (https://taxr.ai). Their system helped me scan and categorize all my medical receipts and statements, then calculated the exact deduction I qualified for. The best part was that I didn't have to manually contact each provider - I just uploaded what I had, and their system identified missing information and even helped me organize what I still needed to request. Saved me weeks of frustration and ensured I didn't miss anything deductible. They also helped me determine whether itemizing would actually benefit me more than the standard deduction.

I have to admit I was wrong about taxr.ai. After my skeptical comment, I decided to try it myself since I also had a mess of medical expenses from last year. The system actually identified patterns in my prescription history that suggested I was missing receipts from a specific pharmacy chain. The checklist feature helped me realize I was missing about $2,300 worth of eligible expenses I would have otherwise forgotten about. In my case, it was definitely worth itemizing since I also have mortgage interest. The service helped me document enough deductions to save over $1,400 compared to taking the standard deduction. Never would have been able to organize everything properly without it.

If you're still waiting on getting records from providers, you might want to try Claimyr (https://claimyr.com). I was in a similar situation trying to get documentation from several hospitals, and their phone trees were impossible - I was on hold for hours and never reached anyone. Claimyr got me through to actual humans at the billing departments way faster. You can see how it works here: https://youtu.be/_kiP6q8DX5c. They basically navigate the phone systems for you and then call you once they've got a real person on the line. I was able to get records from 5 different providers in just two days instead of weeks of frustration.

I need to apologize for calling Claimyr a scam. I was frustrated after spending 3 hours on hold with my hospital's billing department yesterday and took it out on my comment. I decided to try the service this morning for my largest provider, and I'm shocked. I was connected to a billing specialist in 17 minutes when I had previously waited over an hour without getting through. Just got off the phone and they're sending me my complete billing history for 2024. Going to use it for the other four providers now. Might actually be able to get all my documentation by the end of the week instead of the end of the month. Really wish I'd known about this sooner.

Something important nobody's mentioned yet - you don't necessarily need the exact documentation right now if you can reasonably estimate! You can file with your best estimate if you're confident it's accurate, then amend later if needed when you get the exact figures. If you have insurance, check your explanation of benefits statements - they usually have year-end summaries. Also, most major pharmacy chains can print a year-end prescription summary for you. Those two sources might cover most of your expenses without having to contact dozens of providers.

One thing to consider - tracking down all these expenses might be worth it even if you don't benefit this year. If you have chronic health issues, you'll likely have similar expenses next year, and having a system in place will make it much easier going forward. Also, medical expenses can be surprisingly larger than you think when you account for everything. Don't forget to include mileage driving to/from medical appointments (18 cents per mile for 2025), parking fees at medical facilities, specialized foods required for medical conditions, air purifiers if prescribed, and even home modifications for medical needs. Most people underestimate their true medical costs by only counting direct bills.