Re: Where are the younger people?
I think half of the answer is that you are sailing in the off season. For folks who can only take 2-4 weeks off of work per year they are probably going to wait until it is a bit warmer to go cruising. Everyone says that the Gulf Islands are pretty quiet at this time of year, it is July and August when they are crowded. Jonathan Raban's "Passage to Juneau" demonstrates this well because he sails north on the inside passage in April and south in July and talks about the differences.
When I cruised the San Juans last summer most of the other folks seemed to be middle aged, often with kids, mostly in 30-40' cruising boats that were made in the 70s and 80s. It's true that our Catalina 25 (the one that you met me at about a month ago) was smaller than most of the other boats, but rigging seemed to be about the same. I talked to a lot of other cruisers about their boats and didn't run into any with electric winches. That might be partially self selected though, because I tended to talk to those who owned boats that drew me in.
I have many friends in the Seattle area who are in their 30s and enjoy sailing. Some of them own their boats, some don't. They might get a week of cruising in a year since they are busy with work, family, and other pursuits much of the time. Often "cruising" means 3-4 day trips down here because there isn't time to get up to the islands.
You have a rare chance to cruise at a fairly young age for a long period of time. That'll mean that you see fewer other cruisers your age, but it's still something that I know I'm jealous of.
1986 Pearson 28-2 "Elena"