Re: Ideas for a first boat? West coast (BC/WA), day cruising, island camping.
Since you are a few years away I'd say join a sailing club and get time in a lot of boats and see what appeals to you. You won't be renting exactly the boats mentioned here, but you'll be sailing similar ones and get the idea.
You can rent Lightnings at the Center for Wooden Boats on Lake Union, they have 2 of them. If you can already sail then you can just do a check out test with them.
I had a Catalina 25 and it's a good boat. The tall mast version is recommended for around here and does well in our light winds. It is a really simple boat and easy to maintain, meaning you can spend more time sailing. However it and the San Juan 24 don't really pass the "simple to rig" test. They can be trailered but would require a hefty tow vehicle and will take an hour or longer to get the mast up and rigged.
1986 Pearson 28-2 "Elena"