I think it has more to do with the cultural bias we see in America and most "First World" countries in the world today. That is, if you're not climbing the corporate ladder and spending as much money as you possibly can on cars, houses, vacations, having the "best of the best" and you're simply breaking even and chosing a life that's right for you, you're a "cheapskate". As I noted, the nickname of "ultimate cheapskate" was given to him by the corporate media, he didn't come up with it himself.
Frugality and simplicity used to be traits that were valued in this culture. But now they're looked upon as "weird" or backward. The fact that people say "it's not for everyone" with their implication that the caged life is for everyone is incredibly biased.