I feel like I am one of the lucky ones, still have property in Vermont that I can go back to, and there is enough insurance on the boat that I can buy another nice one if something happens. Nothing is perfect, we had to switch property managers late last year (my VT property has five rental units) because we actually lost money for the year, but the new manager is great.
I wouldn't trade our life for anything, we both enjoy visiting new places and meeting new people. In fact, we both think that meeting all the really nice sailors and locals from around the world is the best part of cruising. Right now we are in Vermont for a couple weeks, I am reminded of how nice it is here and that retiring here if I have to stop sailing would not be a bad thing. Then back to the boat in Portugal and into the Med for the summer, Spain and Italy, we have already reserved a slip in southern Sicily for next winter.