Luke -
I like your idea. I would propose the Hitchcock trophy be considered as one of the South Shore events.... The start is out by Boston light and the course is typically long legs out into Mass Bay and back. Perhaps the Constitution or JFK regatta out of Cottage Park could be considered as the other South Shore/Boston events. I am thinking about events that won't require boats that are traveling from the North to have to come deep into Boston Harbor or Hingham Bay.
My 2 cents.