I've thought about this a lot over the last 30 years. I have a couple friends who had been 'live aboards' on sailboats in California, I've met a lot of their 'marina friends'. They tell me "it's every sailors dream to one day retire and go cruise the world", but cautioned me, "it's not for everyone". My buddy Pete, adds "We've know several people who have done it, but about half prepare for it, do a 3 week trip down to Mexico, and decide 'it sucks' ".
On the other hand, adventurous types, like my wife's friends (who wrote a book about their adventures) and a friend from the gym and wife whom I follow on FB, are really having a grand time. But they both have several things in common: Their partners are 'go with the flow' types, they can spend hours on end in each others company and not get tired of their partners, have that 'can do' attitude, and are can fix stuff. When I say 'can fix stuff', I don't mean the stuff I do, I mean can troubleshoot a generator that won't start, can wire up a new radio, can hire out and direct the major repairs and have the back up cash reserves to handle such 'eventualities'.
1995 E350 7.3 Diesel, 4x4 high roof camper, UJOR 4" lift