It also depends on the story you have to tell. I had a Motzei Shabbat flight home from MIA to LGA on AA booked way in advance (I know this is a Delta discussion, but I would suspect parallels can be drawn), and they made the flight 50 minutes earlier. I explained that I had just enough time to return a car to the airport and get to the prior flight, but that it was impossible for me to make the new flight time travelling with my family, bags to check, etc., with the time that the Sabbath ends. Got them to book me on a Sunday flight instead -- which, by the way, was much more expensive had I booked it that way to begin with (Dece 31 versus Sun Jan 1). Took a bit of a lengthy conversation, but it worked well.