I don't like his strategy. If the team is doing really well, then he will want to go to games and may pay a premium. If the team is doing poorly then, sure, he can go to the games for cheap. But neither outcome is very desirable.

I'd rather pay face value and hope for a great season, leading me to feel like I got a "deal." If the season goes south and I feel like I overpaid, that is unfortunate but I know the prices/risks when I buy.