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OrphanWilde comments on LINK: Infinity, probability and disagreement - Less Wrong
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Are you selling the outcome? I/e, "If I rolled a 6, you can have the $1"?
Because yes, both players should choose to sell the option. And likewise, both should choose to buy if their twin offers. Or, alternatively, both players should rationally agree to exchange outcomes.
And precisely because of how the angel assigned the twins, people would be winning on average in this game.
With infinities, this is possible. Just like in the infinite world, pyramid schemes are possible. You can generate free money simply by having each person with number N send $100 to a person with number N/2.