A quick note about the impact of filing for Medicare on HSA plans. If you are still working past 65, and are enrolled in an HSA plan through your health insurance plan, you want to be careful about your selections for Medicare.
Enrolling in any part of Medicare, including enrolling only in Part A, makes you ineligible to contribute to an HSA plan going forward. If the HSA is a big part of your health insurance strategy during these years, you want to be careful about the impact of applying for Medicare.
Remember, when you apply for Social Security Retirement benefits you are automatically enrolled in Part A of Medicare. So, if you are still working past 65, and have an HSA plan, it is another reason to consider delaying your application for social security retirement benefits.