We've been sailing/racing/cruising around Boston for three years, after sailing on Lake Ontario for three. It is challenging and exciting and we love it- wouldn't trade it for anything now that we are used to it.
Weather varies/wind varies....We have a full keel on our 35' boat. You don't really need a shoal draft up here- plenty of deep water. We've sailed from the North Shore to the Islands and Buzzards Bay and race regularly in Hingham Bay. Make sure to spend the money and get a great GPS set-up- couldn't do without one.
As for boats, we've loved our 35' C&C, but are now looking for something a little bigger. Wouldn't hesitate to recommend an older C&C at all, if you can find one. (We'll put ours on the market soon, but it may be more boat than you want)
Good luck on your search- maybe we'll see you out there this summer!