I am glad to see this thread. I am on the cusp at 30, but still seem to be one of the younger generation pursuing this dream. I think that this may be a growing contingent of the sailing community and may be a big reflection on the differing viewpoints the younger generation has than the boomers.
Specifically, we kids are waiting longer to marry, have kids, and no one is dilusional enough to think that our companies are going to look out for us. Urban commnities are not as tight nit as they used to be and families tend to be more scattered. I think all of the above has allowed some us to begin questioning earlier what it is we really want out of life. The younger generation seems to be more willing to buck the status que and go a different way. Personally, I am excited to see it and meet others who are choosing this path earlier. With the advent of groups like ASA and BoatUS sailing isn't the exclusive "old boys club" it used to be. Now if we can just save up the moula flipping burgers to afford that Raymarine ST 60 instrument pack we'll see you in Tahiti!