Always glad to welcome another BCer!
For cruising around our part of the country I'd certainly be looking at the Cal 20s, SJ 24s, Cal 25s, C&C 24/25 etc as a starting boat rather than a smaller dinghy style. You are so close to so many amazing places but you need more of an all-weather type of boat, plus one you can actually sleep on with some comfort.
I daresay if things go well you'll be looking to move up to the 27-30 foot range quickly enough.
Meanwhile, look at lots of boats, read lots of magazines and forums such as this one so you're well equipped to make some rational decisions come purchase time!
Welcome to Sailnet!! And congrats on your recent certs.
I like Faster's advice above. I've only had the opportunity to sail in the PacNW once, but from what little I saw of it, I know I'd want a boat on which I could at least overnight comfortably.
I don't especially like the share/club option, but much depends on your personal circumstances. It can be the right choice for some people, especially new sailors that don't want the hassle of ownership just yet.
On the other hand, you can often expend as much in one year, between join and annual fees, as it would cost to purchase a small cruiser along the lines of what Faster suggests above. If you have a family and want to configure the boat to make them comfortable, owning is really the best way to go.
So keep looking around and weigh your options carefully.
P.S. Ask away with those "annoying questions." Most of us are happy to help.