This is what I was thinking. It doesn't take a CEO's wage to decide it's worth paying $50 to not spend hours optimizing your flight or compromising on a connection or whatever.

Any pricing system where jumping through more hoops will save you money itself a form of price discrimination. The less you're willing to pay, the more time you'll spend trying to get the best deal.

It's the same reason why coupons exist. Someone who is willing to pay more is less willing to spend the time to clip coupons out from the paper.