Re: New boat owner looking for day ride PNW
You might consider buffing out the gelcoat rather than painting. From that photo it looks like only the top stripe is likely too far gone. Painting is a lot more to maintain in the long run.
I'd recommend classes, I think you'll get more out of them than ad-hoc learning while out with others and it will force you to learn safety things like man overboard rescues. The SailNow class at the Center for Wooden Boats could be a good match because you already have motor docking skills down (which is a big part of ASA 10x classes). SailNow only teaches sailing (the boats are motorless keel boats) and does a good job of teaching sail trim and handling. They have classes on Camano Island (Cama Beach) which sounds like it might be a better location for you.
Private instruction also sounds like a good option, and there are many private instructors in the area.
boats that I sail on regularly: Pearson 28-2, Rondar 505, Yankee 30, Blanchard Junior