1) I'm a huge fan of spending 2 nights whenever possible so I would say yes. Save Peter for the next trip.
2) Yes, get a slip. The dock hands are very good at guiding you in. If you're not comfortable docking, ask at the base for someone to show you how to maneuver a large cat. It's much easier than a monohull or a twin engine power boat.
3) Yes, should be a great downwind run.
4) not sure; other will chime in.