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I guess it’s not that different from margin calls in terms of predictability. Instead of leverage levels you’d track commitment levels to structure this trade. You could build a proper trading algorithm fed by DAO treasury trading proposals passing.
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There has to be a game-theoretic solution to unwinding schedule proposals. Obviously “sell 95m worth of ether in 24h” is terrible. Basically a designed flash crash. Make the timing random or extended. A bit like spread-spectrum or frequency hopping comms to avoid intercepts.
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