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Guy find ways to exploit the system - some of it is reasonable, for example taking advantage of airlines overbooking flights, but some of it is just being an ass, for example demanding a voucher if his headset is broken rather than a new headset. Plus, lots of boring multi-leg flights with no real destination just to rack up miles.

Guy should use his brains for something more useful, like solving the traveling salesman problem.

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he's making a lot of money doing what he enjoys and it is legal, so what exactly is wrong with that?

Spoken like a true HN devoté...

In terms that you can understand: legal != right

Correct, but it is still a form of hacking, by way of social engineering. The ethics of it are dubious, certainly, but there's still something to appreciate in Kevin Mitnick types, even if they don't necessarily deserve to be lumped as "hackers" in the sense of technical prowess.

Engaging in human hacking and systems analysis of institutions like this can have high personal pay-offs, but it also often requires to revolve much of your lifestyle around it, so whether it's worthwhile varies.

People who write legislation are not literally deities.

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