We have a condo in Brewster, and I'll probably keep the boat on the trailer at least for this season. I'm hoping to sail in Pleasant Bay (Orleans/Chatham), in CC Bay from some of the beach launches in Brewster or Orleans, some of the many ponds in the area like Long Pond in Harwich, and probably Wellfleet Harbor, although the launch ramp there is scary steep!
Wellfleet is a nice place for a shallow-draft boat. In fact, one of the main reasons I bought the DS was how much my teenage daughter enjoyed sailing a little catboat we rented in Wellfleet. Do you have a mooring there?
Take care,
Mark