I gotta a say Va. is definitely not a bad place to live. The weather is pretty nice over all, the humidity can get pretty oppressive at times, but generally winters aren't too bad and the summers can get kinda hot but it's all pretty comfy. The mountains are only a coupla hours away to the west and the water is even closer, except for the ocean and that's only about 5-6 hours.
For our retirement purposes tho, we plan on living on a boat. The grand plan is to start out doing the 'great loop', which (for our location) is putting in on the ches. bay somewhere, cross the C&D canal, up the coast past NY, hit the Hudson, thru the great lakes to Chicago then gead south to the Gulf. Then over to Fla. and back up the ICW to the bay and cross your wake where you put in. This all takes a year or more, it all depends where all you want to go and how muich time you want to spend everywhere. There's thousands and thousands of miles that are all navigable, it's all up to you. Google great loop, tons of links, but I gave the the basic route.
Might all be a pipe dream with health issues, but I think it's possible.
JOHN
..And it's an awesome dream and a great goal to try and get to.