Software is inherently complicated. If you say to somebody I want an airline reservation system, to really say what you want in terms of overbooking and fares, and different airlines communicating with each or schedule changes, it's immensely complex. And so you can't write a program that's any simpler than that full specification.
The worst sort of business is one that grows rapidly, requires significant capital to engender the growth, and then earns little or no money. Think airlines. Here a durable competitive advantage has proven elusive ever since the days of the Wright Brothers. Indeed, if a farsighted capitalist had been present at Kitty Hawk, he would have done his successors a huge favor by shooting Orville down.
In most instances, at all costs, do NOT check a bag. Especially during the holiday season. You have more flexibility to switch flights, switch airlines or even leave the airport and get a rental car to drive to your next destination. If the airline has your bag, they also have you.
What opened up the American West was the fact that you owned the real estate. You owned the gold mines, the oil wells. The creation of these, back then, million dollar industries drove the railroads and eventually the airlines to provide this kind of transportation.
It was over in a blink of an eye, that moment when aviation stirred the modern imagination. Aviation was transformed from recklessness to routine in Lindbergh's lifetime. Today the riskiest part of air travel is the drive to the airport, and the airlines use a barrage of stimuli to protect passengers from ennui.