This seems like a quick way to make money for CFAR/SI. After all, there are plenty of rich people around who would consider your proposal a guaranteed win for them, regardless of the stakes: "You mean I can say "I win" at any point and win the challenge? What's the catch?"
I'm guessing Eliezer would lose most of his advantages against a demographic like that.
Update 2013-09-05.
I have since played two more AI box experiments after this one, winning both.
Update 2013-12-30:
I have lost two more AI box experiments, and won two more. Current Record is 3 Wins, 3 Losses.