Don, I've lived aboard in the Florida Keys and boated in ever state from CT to south Florida for more than 60 years. For me, there is nothing better than the Florida Keys, however, it is expensive to be a live aboard there, but in reality, no more expensive than living in a home in Oregon, or Maryland, which is where I currently reside. The cost of slip rent for my 33 Morgan Out Island was $753 a month during the winter, which is the height of tourist season. It's a couple hundred less during the summer months and this includes water and electricity. I have a friend who lives in Boston that pays more than that for his real estate taxes in a modest home.
The weather during the winter is usually very dry, and you'll usually find good sailing nearly every day, either on the ocean side, or gulf side, depending upon the wind speed and direction. The waters are beautiful, turquoise color until you get about 5 miles offshore in the Atlantic, where they become azure blue. Temperatures during the winter range 75 to 85 degrees most years, but the past two years have been somewhat cooler, often in the mid to upper 60s.
Recreational fishing in the keys is beyond your wildest dreams. If you cannot catch fish here, you should take up golf or basket weaving - it's that good!
All other commodities seen to cost about the same as they do in Maryland or Oregon. Groceries were no more expensive in the Keys than they were at home. Haircuts were cheaper at the local barber shop, and there is a small hospital in Marathon and a few connected clinics nearby.
I have a friend that lives aboard in Punta Gorda, FL aboard a 38 Morgan, his slip rent is about $550 a month including electric and water. The marina provides them with lots of great things, including access to their swimming pool, restaurants, shopping is withing walking distance, and the live aboard community consists of folks mainly in the 45 to 65 year old category. Every evening just before sunset, they have a dockside happy hour and everyone usually brings some snacks as well.
Having lived in Spokane, WA for three years, it was absolutely beautiful there, but I really missed being near the ocean and boating. When I moved back to Maryland, the very first thing I did after building a new home was to purchase a boat big enough for navigating Chesapeake Bay. Now, some folks will tell you the Chesapeake offers the best sailing in the world - I beg to differ. The bay is a substantial body of water, but you can only sail about six months of the year, and most of the summer the winds are 5 to 10 from the southwest. Summers are hot, humid and sticky. Florida summers are hot, not nearly as humid in the keys, and in reality no warmer than it is in Maryland.
Good luck,
Gary