With the where you are at, the ability to really cruise the NW waters. a mid 20' CB style sailboat would be the best option that is trailerable. Otherwise, it would take you a freaken week if you will to get to the SJ's or equal from where you are. Where as you could be up here, to a larger lake in a day.
I would get the largest trailerable easily setup boat one could.
She drives me boat,
I drives me dinghy!