I just turned 31 this May and this is my third season with my 36' Dickerson ketch - she is from 1963, and wooden, so most of the conversations about her involve my jokes that "I hope she is still floating", but it's been a blast so far. I am spending the time to do a lot of the work myself, but here in Maine we got 11.5 inches of rain in June (avg is 3)... so needless to say it took awhile to get all the varnishing done this year (outside at the yard). Truth be told, the work is almost as fun as the sailing, if you have the right attitude. Doesn't make getting up in the morning to head to the boat yard any easier, but it could be much worse.
As to the limited number of young people sailing these days - I do think there are a lot of people who just don't realize how cheap it can be. With this economy, I'm seeing plenty of boats for a $1000~$2000 that are in good shape, often trailerable (or with trailer!), and ready to sail - pocket cruisers, day sailers, and even coastal cruisers, you name it. It can be done cheap if you have the patience to look for the deals.
Around here one of the major problems is getting a mooring - there are waiting lists between 5 and 10 years long in most towns, and renting at a marina is highway robbery. Another reason to get a trailerable, I guess.
When I do it again I'll probably go smaller (and very probably not wooden!).. but I had to make the mistake once in my life so I would know better in the future