That'd I would so do that. I would love to help out with that or even host the event. I'd soooo host that. I could set it with the mock combat and everything having martial arts and mock combat experience.
That'd be good if there were 20 experienced cosplayers/mock combatants that'd be willing or the possibility to train said 20 people as well as hold the actual chess match within the span of a couple of hours. While it seems like a fantastic idea without time being an object, we would have to fit cosplay chess within the time constraints of the convention. Awesome idea if we had the time to do something like that, but doing it with a 2-hour time constraint could prove to be an issue.
The only legit way I could see it even remotely happening with our current con layout is if it's shown in the tent via projector, live streamed from one of the larger panel rooms where it would actually be happening. While this way would cause the least problems, it presents its own issues. People walking in on the chess match, the fact that live streaming it could prove difficult (unless Tech-Ops could manage it), the fact that it would be the ONLY event that takes up two rooms, thus cutting down on alternative programming.