Sounds like you'll have fun this summer locally in Oregon--and then, no problems finding ways to get out on boats in Hawaii. Suggest you get yourself linked into a couple of the yacht clubs on the US West Coast that might have members who need a hand going to Hawaii. That is a summertime trip usually so you might be able to even get a ride this summer. The SoCal clubs are going to be more likely to have something for you. Put an ad here in the Crewfinder, too.
Once you're in Hawaii, hopefully you'll also link up with some local clubs there too. We have a couple members in Hawaii, I hope they'll come along and welcome you--though they might be out enjoying sailing