Through skype and email we were able to answer a few questions yesterday.
Kent County, Md. tells me we can get by with a three day non-resident permit to use their ramp in Rock Hall. There are places where I can purchase the pass in town, but most likely will apply in advance through the mail and have the permit in hand to save time on launch day.
Researching Chesapeake City, which Bruce and I agree is well worth visiting, I found that they have public docks available at no cost for overnight stays. I believe the docks are those to the left in the photo above, next to the park. An easy walk to the small downtown and the Tap Room Crab House which offers, from the looks of their web page, a meal much like the one we had last weekend (I forgot the shrimp). That will give us a choice of two places to eat - the more upscale looking Chesapeake Inn or the more family style Tap Room.
Bruce and I skyped last night to go over the route and a few other details. We are leaning towards sailing across the mouth of Delaware Bay to Lewes and then going "inside" at Roosevelt Inlet (this would be the lighter blue path marked below) and taking the canal down to Indian River Inlet (marked in red).
Our goal will be to reach either Chincoteague or Wachapreague. Both places have docks, ramps and nearby hotels for the night we get in, plus rental cars available in nearby towns (though I need to call and confirm that they'll pick us up).
We've got about a month until the trip.