This is such a great post! And so timely!!!!
You add all your deductions and if they are under $12,000 (single)/$24,000 (married), then you just claim that amount and forget itemizing things. Itemizing is worth it if you exceed the amount you can claim for ALL deductions together.

Here is some great info from Turbotax:

A general article explaining Medical Deductions:
https://turbotax.intuit.com/tax-tips/health-car...

A list of what you can itemize as medical deductions such as insurance premiums or acupuncture or what Inthegrey listed.
(Some on that Turbotax list made me laugh, like the "clarinet and lessons to treat the improper alignment of a child's upper and lower teeth").
https://turbotax.intuit.com/tax-tips/health-car...

Other deductions according to Turbotax:
Other deduction examples include mortgage interest, state and local income and property taxes, said medical and dental expenses, and charitable donations.
You would file your income taxes using Form 1040 and list your itemized deductions on Schedule A and copy the total to the second page of your Form 1040.
This amount is subtracted from your income for your final taxable income number. But only if that total is bigger than the 12,000 (single) or 24,000 (married) that you can claim automatically.

My neighbor is a CPA. He says yes I can add up all our out of pockets including the items you named. However the standard deduction went to $24,000, so we have to have spent $24k over the 7.5% of our AGI in order to make itemizing better than taking the standard deduction. (We can deudct any expenses *above* 7.5% of our AGI.)

So I met with my accountant this evening. I file as single and didn’t work last year, just investment income that was not taxed at Federal level. Even with $20k in medical expenses plus my other deductions, the standard deduction was ok, but we itemized on state (NY). I owe zero😊.

Although, I may backdoor some IRA roll over to a Roth - a good opportunity to do this since I didn’t work. Taxes will be low to do this.

From what I’m reading you can. I meet with my accountant tomorrow night, I was gathering all the info. I just read this on CNBC

“The tax overhaul temporarily lowered the threshold for the medical expense deduction.
For the 2017 and 2018 tax years, you're able to claim an itemized deduction for out-of-pocket health-care costs to the extent they exceed 7.5 percent of your adjusted gross income.
Starting in 2019, that threshold will leap back up to 10 percent — where it had previously been for most taxpayers. Bear in mind that while the IRS has lowered the bar for the amount of medical expenses you must incur in 2018, fewer people all around are likely to itemize their deductions due to the higher standard deduction.
As a result, this break may no longer be available to you.”

@A MyBCTeam Member you are so right. I still should add up my medical — though we won’t have much *over* 7.5% of our AGI — and then add it to all the other allowed deductions and THEN see how it compares to standard deduction of $24k for hubby and me. Our property taxes where we live are low, but added with mortgage interest (we pay way less of that than we did a decade ago...) and the insurance premiums that are taken out of my check Post-tax (which don’t amount to much comparednto my medical premium, which is taken out of my pay per-tax and therefore not eligible.),...maybe we would have more than $24k. What a chore!

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