I could say, sounds like the beginnings of a well laid out PLAN! Or better yet, IT'S ABOUT TIME! I'm getting excited FOR you, since I have already experienced long distance cruising in both Sailboat and Trawler and know full well how exciting and rewarding it can be.
Don't know how much time you have available, but you might want to consider a circumnavigation of the DELMARVA Penninsula while you are at it. When you leave VA just continue out the mouth of the Chesapeake and turn north up the coast to Delaware Bay or wherever. Just a thought.
Since I've transited the C&D Canal a few times, recommend you check the local TIDE and CURRENT tables and diagrams for the most advantageous timing of your trip. The current can be strong, and you will want TO GO WITH THE FLOW as they say.
Launching at Salem you will not have to concern yourself with the tides and currents in Delaware Bay UNLESS you do the circumnavigation mentioned above.
The Chesapeake is a marvelous body of water that I sailed for nearly 20 years cruising its entire length in daylight and at night (with RADAR).
Summer (June-July-August) is too hot and humid often with very light to NO wind and strong thunderstorms. Winter is, of course, out of the question. Spring and Fall are quite nice on the Chesapeake. If I were considering such a trip I'd check the historical weather data again for around April-May and September-October-November and go from there.
Allow enough slack in your schedule for lay overs, at marinas or on the hook, on bad weather days. IF YOU ARE A SLAVE TO A RIGID SCHEDULE YOU'LL WIND UP DOING SOMETHING STUPID!
What you have in mind is definitely NOT a "fool hardy adventure", but rather an attempt to make a reasonable dream, nurtured by the strong lure of the sea, come true.
Bon Voyage & Bon Chance!