I like Hopkins. Since I fly in and out of here multiple times a year I feel like I can navigate my way through here pretty easily. I like how you get drive right up to the entrance and walk right to the baggage check line and security - I am sure I could do this at O'Hare or Midway in Chicago if I had rides to the airport but the distance from the train to the terminal is insanely long. The security never takes too long and everyone is generally pretty friendly. It's also small enough to easily navigate but not too big that you need to shuttle or bust out a map just to get from point A to point B.
Just remember:
1 - It's not the AIRPORT'S fault (generally) that you are delayed, get laid over, or miss a connecting flight - most of the time it's an issue related to a late departure from another airport or a weather incident.
2 - Fly Southwest into Cleveland if possible. It's much much much closer than Continental and you don't have to walk a mile to get your bags at the baggage check.
Happy travels!