I've been lucky,
I can fly through BWI from my home airport and land around 11:30 or fly direct from BOS and land around 12:30 (this year-it keeps changing year to year). So my biggest problem is whether my ride is on time and my room is ready when I arrive.... so far, only 1 snafu last year with my ride (JUTA).
Last year, i set my alarm wrong. Luckily I was flying from my smaller home airport. I was supposed to fly out at 5:30 am and woke up at 4:15 am. Needless to say, thanks to being a smaller airport and first thing in the morning, as well as an attentive desk agent, I made and my luggage made it... that's about as close a call I ever want!!!