My own anwers are:
A) Yes
B) I'm thinking either June or September. Only after this whole COVID thing blows over though.
C) I was thinking Mt Hood was most centrally located between OR and WA. I know there are a lot of places to go up there but I'm not local so I don't know any specific ones. Alternatively maybe Astoria or Long Beach. Long Beach has the benefit of a 26 mile long drivable beach. And although I hate the movie "Goonies" we could create the opening scene.