Haven't done it in a couple years. I'm from western Mass., and drive to Westport CT and take MetroNorth into the city. After the ride, take the train back to Westport and home. Makes for a very long day. But the ride is a blast and I think it's worth it. At least I plan on doing it again this year.
My wife and I plan on doing it this year, for the first time, and I have the same questions. Guess will find out. And in addition to getting us into and out of the city, my kids, 15 and 18, decided that they could wander around Manhattan while we ride. Don't know about that either.