During the year keep a running tab on how much you have spent on all medical costs including prescriptions, doctor visits, dental visits, co-pays etc. I also keep my statements and receipts together with this list in a folder. At the end of the year, you already have a total without any additional work. Now you can add it to other items you can claim as a deduction (property taxes, work related expenses, etc) to see if it is better to itemize- or to take the standard deduction.
Source: My own tried and true idea that I have been doing for many years
To actually get a deduction for medical expenses, they have to exceed 7% of your annual income. So, if you are getting close but not quite there, it may be time to buy some new glasses or make an appointment you've been puttin off. If you're not near 7% by the end of the year, you may want to do those things after the first. Of cours, you do have to consider whether you've met your insurance deductable.
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