I think the problem is with the assumption that expected wins are a good guide of behavior at the granularity of individual plays of the game.<p>The expected win is infinite because very rare scenarios have huge payouts.  However, any one play of the game has a 50% chance of paying out nothing.  If I get to play the game a large enough number of times for the rare scenarios to actually occur, then I would be willing to pay a higher price than if I only got one shot at it.