I figure the answer to this question is "probably not," but figured I'd ask the experts.

Flying into DTW from Madison, WI (MSN), flying back out to NYC. I'm 99% certain my flight out is the last of the night to the NY area. Should I just expect an overnight at DTW? (EDIT: This is early next year, not today - I'm asking just to be prepared for likely difficulties.)

I normally wouldn't consider such a short connection time, but honestly - the fare was astoundingly cheap, and I don't really care if I'm late to work the next day.

Assuming I do miss the flight for non-weather-related reasons (say, delayed takeoff in Madison due to bureaucracy or whatever), any chance DL will put me up for the night? Or would they possibly hold the NYC flight for a bit to accommodate me?

Thanks for any thoughts!