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Love the Chesapeake

Assuming you're gonna live somewhere near your work, The Magothy is probably your best bet. Spent 20 years there with my boat at the community marina. Problem is there are not a lot of public marinas.
I would stay out of Annapolis except to visit, too much weekend traffic both on land and on the Severn.
Currently my wife and I live in Baltimore but I would never keep a sailboat there. It takes 2 hours to get out of the river. We keep our boat in Herrington Harbour South (about 20 miles South of Annapolis, near Deale) one of the nicest marinas anywhere. It also is centrally located meaning both the mouth of the bay at Norfolk and the head of the bay at the C&D canal are within reasonable distance. I'd rather drive the hour it takes me to go the 50 miles from my hous eto the marina and then be on the bay when I get out of the marina than spend 2 hours dodging container ships in the Patapsco River.
The Chesapeake has literally thousands of miles of coastline with quite coves and small towns everywhere. Oxford, St Michaels, Gratitude, The Corotoman River, the Solomons, Tangier -- I could go on forever. It would take me two lifetimes to see them all.
As you surmised, you're gonna need light sails, 140-150 genoa, cruising spinnaker for cruising. If your race you'll need a full suit of light sails.
As a bonus we have the Chesapeake Bay Blue Crab
Hope to see you on the bay
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