Al, welcome to the site. A trailer/sailor is a great suggestion although, if you are retired at anything approaching the normal age, the lack headroom
may prove to be a 'pain' for anything more than day sails
and the occasional overnight. This of course is to say nothing about the need for a suitable vehicle for towing - a costly proposition to both purchase
Chartering is a great idea for two reasons: firstly, it will give you an opportunity to see if spending expended periods on board is really something that interests you; secondly, to scout potential areas for relocating.
You just may find that you will not need a condo - that you are perfectly happy living aboard
a boat (and if not full time, at least part of the year). An added advantage to a larger boat is that it will give your family/friends an opportunity to share in your new life. Finally, as to locations, you may find that locating a boat in a warmer climate will not only enable to use your new purchase
year round, but will provide a nice destination
and friends to visit. You may even find that the grandchildren (and your friends) will be lining up to spend time with you - and 'quality' time, since the small world of a cruising boat is conducive to conversation and the sharing of new experiences.
Anyway, good luck in your quest.