Re: Norfolk, VA to Boston delivery
I brought my 35 footer home to Mystic from Florida a number of years ago. We came in at Beaufort, NC and stayed inside for a while with a stop at Annapolis. The trip up the Chesapeake included a harbor of refuge at Pt. Lookout. Beating past the Potomac in NW winds in the upper 30 kt range got old real fast. Yes, you do want to consider the wind forecast. With a new boat, you might want the Chesapeake for a proper shakedown, as someone else mentioned. Annapolis is a good place to look for repair parts. I got a new belt for my AP there.
From Annapolis, we went through the C&D Canal and then to the Cape May canal. From Cape May we went directly past Montauk and into Fishers Island Sound. In your case, you would head for Block Island and give yourself a break. From there I would head for Buzzard's Bay. Depending on your endurance, you could stop at Cuttyhunk (short day) or Onset just outside the western end of the Cape Cod Canal if you needed to wait for a fair current.
Going outside Cape Cod instead of the Canal? SVAuspicious can't be serious. You do need Eldridge's to work the currents. from Block Island until you get past the Cape Cod Canal.
I made the trip from Cape May to Mystic in 2 1/2 days in mid May and motored the whole way, due to light air. The shipping was not the problem I expected, but you do need competent watch standers.