Re: Relocating from Chesapeake to New England
Why not keep the boat in Maine? The best cruising in all of New England and mooring/slip charges and storage charges are probably less than the Boston, Buzzards Bay and Narragansett Bay area.
I live in Rhode Island and keep my boat in Narraganset Bay but we usually spend 1 to 2 months each summer up in Maine and Canada. Lots of great anchorages that are much less crowded.
Take a look at "A Cruising Guide to the Maine Coast" 5th edition or ActiveCaptain.com for marinas. I'd locate in either Penobscot Bay or the Mt. Desert areas.