I think medical insurance from 62 until 65 was the biggest bother I had. One thing that helped was that I had zero income, so I qualified for MediCal (same as Medicaid). I think that was a little too good of a deal (i.e., somebody else was subsidizing it probably a bit too much). Once you can start on Medicare everything is fine again. It took two tries to find the right supplemental medical insurance. United Health Care meets our needs well.
