Re: Norfolk, VA to Boston delivery
I see one glaring problem with your pro/con list above and that's a heavy emphasis on the availability of rescue. Offshore trips should be planned as if rescue was not a possibility. Make sure you and your craft are ready for the trip. If you aren't, don't go.
I note that you seem to believe that you will encounter shipping near the coast but not offshore. If this is so, you couldn't be more wrong. You will be crossing two very busy in- and out-bound lanes, as well as encountering a ton of fishing activity. Add to that the fact that in the spring you stnd a good chance of encountering fog and you are setting yourself up for at least a very unpleasant passage.
If you are concerned about being on a lee shore, just avoid leaving in those conditions.
Don't be what I call a "mighty man of the sea" and leave on a schedule. Wait for a decent weather window for your trip. And take the best route. Treat it as something to be completed within a set time and you open yourself up for all kinds of trouble.