First off how much are you planning to spend? Half a Mil, Quarter Mil, 100K 20-30K? Your budget can help determine the options available.
One thing for sure if your planning on living aboard I recommend you get in as many sailboats as you can before settling for something. That was some of the best advice I got, and I highly recommend it to you.
An A.S.A. Certification is probably your fastest way to go from knowing virtually nothing to being able to sail offshore with no power and only a compass from one inlet to another while sailing through the night to get there at that. Not that I would be stupid enough to recommend it, I was however stupid enough to do it. Another crazy surfer and me managed to pull it off, looked at it as if it was a 27' surfboard instead of a Tartan...
Captain giving me the lessons, said I was not ready to sail on my own yet, He was right, had not everything that could have gone right managed to go right we could have been in trouble...
I found a couple of quote's that hit me to the core while watching the movie White Squal, 'Sailing is not a game", "A sailboat is not a toy', and "without order, we have nothing..." Those are some serious words to live by... It happens and when it does having had done everything you could to prepare for it, may be the ultimate difference between survival...
I highly recommend and ASA Course... A few hundred bucks will not only save you years of trial and error, but maybe the lives of you and yours and others who could have been impacted by you learning the simplest of proceedures the hard way.
Sailing is amazing I love it. Sounds like you will too... Here are a few sites to help get you started... I am still a green horn with less than a year of sailing under my belt, there is a lot ot learn, electrical, mechanical, navigation... Knowing how to sail is the tip of the iceberg, knowing your boat from every inch is also a huge... because when you have issue's out there your probably going to be the only doctor, electrician, carpenter, mechanic... You get the picture...
Time for you to get busy, I recommend two books the 12 volt Bible and Sailing Fundementals its an American Sailing Association 9ASA) learn to sail manual. Hope that helps
Welcome to Seattle Sailing Club
List of sailing schools in Washington, Oregon, Alaska and British Columbia
Here is a 30' boat with a trailer for 30K in Portland, lots of other boats here to browse through be sure to read up on as much of them as you can to get an idea of what your are getting into and what the market is doing. The more info you download from looking at these the better imo...