They're already there,...in vacation homes, living on or near the water. When they want to get somewhere, they fly first class. To compare daysailers to cruising boats is to compare hydraulic back hoes to garden trowels.
Daysailing isn't new, is it? Sailing wasn't always just a means to and end as it is in cruising. Sailing has always been an end itself in the form of daysailing, racing, messing about, etc.
I don't think the next generation of adventurers has to worry about boats. As I age, I row by more and more boats that have outlived their owners, some, several owners. At least that's true of the well built ones. The junk boats will slowly disappear, as they always have.