I bought my boat last fall and moved her from Stonington, CT, to Kilmarnock, VA, over Halloween. Right at the beginning of the window you mentioned. Weather for the most part was delightful. My boat is definitely ocean going, and were I to make the trip now, I'd wait for a good off shore weather window and go directly from RI to Cape May and up the Delaware and down the Cheasapeake Bay to ICW, or better, straight to Cape Henry (always have the option of cutting in at Cape May) and then ICW. Overnight run from Morehead City to SC.
I did take Long Island Sound-NJ shore-Delaware Bay-C&D Canal and Chesapeake Bay route because the boat was new to me, and when there were strange noises or bumps, I was not sure where to even begin. So caution ruled. Just wait for good weather. I had to hole up one day at Manasaquan owing to a crew member becoming ill. The weather was really rotten coming out of Raritan Bay and dictated waiting. Should have waited at Staten Island or Atlantic Highlands. Another lay day at Cape May as the wind (20 knots) was coming from the North down the Delaware Bay. Just no fun. We waited a day, enjoyed the town, caught a good tide next morning, and ran from Cape May straight (28 hours) through the C&D and Bay all night to Kilmarnock. So, out of seven days, 5 good enough for passage making.
Two words of prudence: marinas along the way are shutting down or limiting service hours, so cheack all that as you do youre route planning. You don't want to find youself needing to duck in for some reason to discover the place is closed. And the second word is when planning your runs, make sure you keep track of daylight hours if you plan on heading for shore for the night. You are losing 20-25 minutes a day of daylight.
Cool at night; pleasant in the day. Sweat shirts.