This is sort of answered in the main wiki post but I have another "should I book this connecting flight" question:
I have a flight arriving on a Sunday afternoon at 15:35 on Iberia (in PE so I won't be the last one off the plane, either). I have Global Entry and will just have a carry-on bag. I have two options for a flight back to TPA the same day, one at 17:45 and another (much more expensive) option at 19:56. Should two hours be doable there? This is obviously making a big assumption that my flight back to the US is on-time.