I'm trying to get the base built by the time the weather gets good, so I can just work back up to fighting trim between March and April-ish. It's deceptive because all the riding around where I live involves constant stop-and-go from light to light. I imagine it would be a lot easier to cover ground going non-stop along decent roads.
I am, of course, game for the Hambone Hundred (I believe, depending on when exactly it happens.)
My girlfriend has said she would be happier if I did longer rides as part of an organized event, so I think Montauk would be a good way to get in the century, not have to bring a lock and endless food/gel/whatever.
Also, I would think that once you work in going to the point and back, you almost have a double metric, right?