Echo the endorsement for San Juan Sailing. I have recommended them to several friends and relatives without disappointment. Their big asset is location. Easily accessed from SeaTac without ferry rides and border crossings. Two hours after landing, you can be sitting on your boat! If you can take a border crossing and/or ferry ride, the Bosuns/Seahorse operation in Sidney, BC is a nice place to start from also. And they are priced in that other currency!!
Favorite islands and anchorages??? Geez, have had a boat up there for 15 years, very seldom go the same place twice!! Depends on your tastes in cruising. Is it an evening sitting on the hook with the crab rings set (Westcott Bay), or, China Town in Victoria''s Inner Harbor moored in front of the Empress. It is all time related, everything is within a 30 mile radius of Friday Harbor. How much time do you have, Dave?? A Fantastic cruising grounds.