Not thrilled about the idea of trucking it north or sailing the Washington coast this time of year.
Not too far to truck a boat, and all of our YC members with trawlers routinely have their boats trucked to and from Olympia for vacations, since trucking costs by the mile.
FWIW, If you find a Good boat, and avoid the costs of "deferred maintenance", a few trucking dollars and the re-launch in the Sound will be cheap.
Note that if you buy a boat in Portland, after the survey it could be loaded directly onto the boat hauler's trailer.
Up the coast, it's less than 30 hours to the Straits. We'd need a weather window and the blessing of your insurer. The owner of this Ericson and I have probably done this trip 15 or 20 times, in boats smaller and larger.
Just something to consider.......