Most insurers will have age limits but there is the odd one that will insure up 99 years old BUT unless they contractually agree to a set percentage rise each year, once you get old they can simply ramp up your premium to an insane level to get rid of you. Point 2 - I've never heard of an annual medical being covered, apart from the initial medical which is their interest. Also do you really want them to get an update every year on you which could whack up your premiums? Best to get it done seperately and privately in my opinion.