I am coming from farther away than you, but a couple of factors I considered were
- traffic is way less on the Eastern shore. More scenic driving too
- cars go 60 mph. boats go 6. I would rather drive a little longer and be closer to the good sailing areas than spend an hour or two trying to get to decent sailing places every time I get to the boat.
Given all that I have my boat in Rock Hall. Nice little town too and not far from Baltimore, Annapolis, St. Michaels and about a thousand decent anchorages.