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.
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.
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.