I would not leave the Puget Sound waters with either boat until each of you learned to sail YOUR sailboat well. There is so much to learn about sailing that you NEED to learn completely. Where are you going to moor your sailboat?
The entire Puget Sound area is difficult to find affordable moorage. You might think about securing boat moorage BEFORE you purchase anything. If you are thinking about a liveaboard vessel, purchase the one with the most interior storage and plan on renting another storage facility to house all the articles you can't bring onboard. Either the SJ 30 or the Islander 30 would be fine to learn to sail in the PNW waterways.
There are many vessels available in the PNW. You might also keep an eye out in the Portland metro area. Boats are several thousand $$ cheaper there. Keep looking a while longer until you have seen the Good, the Bad & the Ugly boats in your area. You will know which boat is for you after the survey is complete.