I have a novel plan for the AI player that I believe will work against most gatekeeper players. Even knowing how it works, it would work against me! It isn't quite ready, but I'd like to know if there is still interest around the topic before finishing work on the preparation.
There's enough incentive for both players to play well that I don't think that we need to involve money. (I'm also very reluctant to send money to strangers on the internet!)
We would be playing under Tuxedage's rules: https://tuxedage.wordpress.com/2013/09/04/the-tuxedage-ai-box-experiment-ruleset/.
Edit: I have finished preparation, and I'm now scheduling the time with the Gatekeeper.
Edit 2: The game was a Gatekeeper victory (i.e. I, the AI Player, lost). Read about it here: Gatekeeper Victory: AI Box Reflection.
I think I already replied to this when I wrote:
I just don't see how, in a real life situation, disconnecting would equate to freeing the AI. The rule is artificially added to prevent cheap strategies from the Gatekeeper. In return, there's nothing wrong to adding rules to prevent cheap strategies from the AI.