Some travel considerations when the destination is too far to be close and too close to be far:
I used to fly to one of my upcoming gigs but after getting stranded in an airport for the amount of time in which I could have driven the distance, I vowed never again to fly. The security hassles added more time to "the airport experience" and also tilted the scales.
Another factor comes into play: control. I once had a training schedule that put me in a different city every day. I'd teach a bunch of managers and supervisors, then rush to the airport so I could fly to another city and do it all over again. On occasion, however, I could simply rent a car and drive. I could train in Boston, drive to a town outside Boston, drive to New Hampshire, and later drive to Maine. It was marvelous because of the scenery and because I didn't have to worry about canceled flights.
I still have occasional doubts about the amount of time spent on the road but they are erased by the allure of an open road. No airport has quite the same appeal.