Unless you have no interest in learning
"offshore" sailing I think you should seriously consider hiring an experienced skipper
to teach you what you feel you're lacking while delivering your boat down the coast. Perticularly if you watch your weather
coast can be traversed with relative ease. Many people in far lesser boats than that OutIsland make the trip every year with very little "experience". Also, I dont think "Offshore" neccesarily means "harder" I can assure you that the things you wont encounter 20 miles off the pacific coast are tidal gates, drying rocks, narrow channels, dense commercial
traffic and massive anchored beds of bull kelp. Those are all things that you would routinely deal with in the Strait of Juan De Fuca and the Puget Sound
I know a young man in Portland
who has done deliveries from The sound to Portland
OR (Including the treacherous Columbia
river bar) and done so with owner crews who hired him to teach them. Time at sea is the only real way to gain confidence and learn "offshore" sailing.
That said, if you dont have an interest in learning
this stuff I wish you the best of luck trading boats.
Remember, there isnt anythiing you cant do it you put your mind to it.
Dont let the sometimes highly dogmatic sailing community convince you that you cant do this without a 100 ton ticket and 100 years of experience on square riggers around the horn. There are many good books
that you can read to help you fill in any specific areas of knowlege you may feel lacking in.
Dont worry about being called "foolish" by bulletin board sailors :-)