OP here. Decided to fly CO from EWR to MEX at 5:45pm and spend Friday evening at the MEX Hilton which is right in the airport. I’ll then take the 9:00am AM flight Saturday morning. This works out well as I will now arrive Merida fairly rested and have most of the day ahead of me. The original flight did not arrive until 4:00pm. I still have a 1 hour connection in MEX on the return on AM flights (into JFK), but I spent the extra miles and am going Business Class on this segment. Besides, if I misconnect on the way home from vacation… who cares!

Thanks for the replies to my question, very helpful responses.