Your idea of a house and a smaller boat is really good. About the "significant other", you've been married. You know that what most women want is stability / security. A guy living on a boat is a fun date for a bar fly, but good luck finding a significant other that finds it attractive. Even if they pretend, you can count on the boat getting sold will be priority #1. Now a guy who owns a house AND has some toys like a boat is a catch. You've mentioned 'at comparable cost' a couple of times. They're not. Boats are big holes in the water that suck money out of your wallet by the thousands. Very little loses its value as fast as a boat or costs as much to maintain. You mentioned cruising up the coast....and burning 30 or 40 gph at 20 kts. A 100 mi trip takes 5 hours+ and 200+ gals of fuel. That's 1.5 hours and maybe 5 gals. of gas by car or 2 hours and 10 gals. by motorhome. One other thing about that significant other. You think apartments have thin walls? Try living on a boat with your neighbor 4' away for a lack of privacy. I've worked on boats most of my adult life and the one thing I've learned is that the best boat is the one your friend owns. You show up with the beer and leave the hassles and expense to him. There really is only one good excuse for living aboard a boat, and that's an addiction to boats and salt air. It does get in the blood for some guys (but much fewer women).