The OP has two issues really. First, being in their 50s still they are probably not Medicare eligible nor Tricare for Life. That does make it necessary for careful study. Then, when a military retiree reaches age 65 and becomes eligible for Medicare and are enrolled in Tricare for Life, it becomes easier. My wife and I are above that transition age, have Standard Medicare and Tricare for Life for medical and drug coverage. The Villages Health System does indeed accept that medical insurance combination and has for a few years. Before then however, we just had Tricare Standard (I think that was the name back then) and it was a little more difficult to find doctors but certainly not impossible; and, no the Villages Health System did not accept that for medical coverage. I caution the OP about enrolling in some of the Medicare Advantage plans when you get to that point; some of them include the drug coverage which can mess up your Tricare drug coverage. As someone said, do not give up your Tricare coverages - once surrendered, it's very difficult if not impossible to get them back.
The suggestion to talk with SHINE is a great one. And of course access the Tricare web site as well. Don't wait too long as you don't want to get into a panic mode when the decision must be made. The time from mid-50s to "retired" age goes by quickly.
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