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.
Very strong upvote and agreement from me. I think people are underestimating just how great a restriction ML-style boxing applies on an agent. There exists an intelligence level at which all these tricks become useless, but before we get to that point, boxing would likely allow us to safely use mildly superhuman AIs to do things which might be pivotal. And each additional trick we discover increase the threshold of safely wieldable intelligence.