Medical deductions are the least useful of all deductions you can take as itemized deductions because they have a 10% of AGI limitation before they become deductible. Medical may help on your state return even if it isn’t useful on the federal. In AL the AGI limit is 4% for 2015. However, some people will still benefit because of the new out of pocket limits made standard by the NOT SO ACA. Most folks keep up with checks, or prescription receipts, Dr receipts and so on. That is a good idea but here is a secret. Auditors prefer the annual print outs that are available from your pharmacy or health care providers. I personally think it is more laziness than anything else on the auditors part but it doesn’t really matter. Those reports make their job quick fast and in a hurry and when you are being audited that is a good thing. So get the reports and log your medical miles too https://www.tmicpa.com/mileage/. One other thing to consider to maximize this deduction is bunching your medical expenses into a single year when possible.