I think some may leave under the “been there, done that” perspective. But it appears to me that situational changes drive a departure from sailing or boating generally. Job relocation, sudden loss of income, health crises, developing decrepitude, break-ups followed by new relationships, degradation of the boat from lack of maintenance, and so forth. Thinking up new ways to enjoy the boat could resist the “bt, dt”exit. Join a club, make new boating friends, go on organized cruises, relocate the boat to a different marina for a time, etc. But if it becomes “unaffordable”, or becomes of poor recreational value through lack of use, then it’s harder to stay in.
Also, we’ve thought about “passing the boat” along but I personally doubt it would end as we would hope unless that person is already into sailing or boating. It’s rather like leaving your Steinway to someone with the hope that s/he will learn to play it and enjoy, versus leaving it to a pianist who really needs a better piano and who would use and appreciate such a fine instrument, well cared for.