By all means radio in dinner reservations. You will definitely need to make them for Cooper too. Use any name except the name of your boat, for safety reasons, so that anyone listening in doesn't know which boats are deserted at any one time. Taxi at Leverick can be arranged once you've docked as long as you are happy to wait half an hour or so. For JVD, check in the cruising guide, or ask at TMM. Not a lot of choice of taxis there.
Itinerary sounds fine, but doesn't allow for much flexibility for weather or just enjoying somewhere more than you expected.