I commute out of Colorado Springs and it has been relatively easy. I have been driving to Denver (I live on north side of the springs) and taking Frontier or ATA. Out of Chicago, there are several lines which are fully commutable on both ends. In march, I have to be at work by 1630C so I take a 10:45 in the morning which gives me one backup flight. I get back to MDW the third day by 2145 which allows me to catch the ATA 22:21 flight home.
America West has put some 737 service back in to Colorado Springs to Phoenix so I will be going back to Phoenix to try that commute for a while. Phoenix, however, does not have many lines fully commutable because the latest flight home is 2130. They have one or two that's fully commutable, but most lines are partially commutable. But the hotel situation is great, 35 a night at the Best Western. I personally am sick of crash pads in Chicago, so this will be a welcome change.
ATA, Frontier, and America West is hardly like flying off-line. They all are extremely good to us, and once we get back in the cockpit jumpseat (this summer, I've heard is the target), then it will be pretty much the same as flying SWA. Hope that helps.