Have the same dream and working it through. Selling current boat and new boat comes in April. Have gone down to Carribean looking at various islands to "home port". ( just got back from USVIs- sailed with a liveaboard couple on a Skye 51 for a day and learned some). Have worked through budget/insurance/mail/residency/taxes/communications/legal etc. Selling house but buying small pied a terre in states so still have a "home" on land. Still working out options for hurricane season. Only advise is go step wise if you can and listen closely to folks who are already "living the dream". Look at your next boat as the boat you BOTH can single in any weather and you can sail when you are 80. Think if you are going to go coastal then Bahamas then eastern carib. or ARC to BVIs or the ditch or one shot to Carib. Think if you may ever want to do the pond or other blue water. Every time you buy and sell a boat it's a PIA and from what you say like me this is your "last boat". Best of luck.