He's really undervaluing his time and energy. Maybe this is a fun and exciting game for him, but I'd think someone as clever and determined could do something more productive.

And that's just /earning/ the miles, never mind using them. I have 1.4 million miles because even the act of using them consumes a lot of clock time and usually turns out a waste of energy (tickets based on mileage are rarely available for the routes/dates I want to fly).