By the way, wouldn't Omegle with the common interests specified as AIBOX basically do the trick?
For the basic interaction setup, yes. For a sense of community and for reliable collection of the logs, perhaps not. I'm also not sure how anonymous Omegle makes users to each other and itself.
AI Box Experiment Update #3
Tuxedage (AI) vs Alexei (GK) - Gatekeeper Victory
Tuxedage (AI) vs Anonymous (GK) - Gatekeeper Victory
I have won a second game of AI box against a gatekeeper who wished to remain Anonymous.
This puts my AI Box Experiment record at 3 wins and 3 losses.