I was in Kumori's cosplay chess game this past year and thought it was very well coordinated. Both the audience and players had a blast.
Kumori does have their rules and sign up online as does Sakura-con (
www.sakuracon.org under the programming tab here:
http://www.sakuracon.org/programming/chess_rules.php)
I have been a co-coordinator for Sakuracon's cosplay chess game for about 4 years and we now have 3 cosplay chess games at con. A Saturday main game that is scripted, A late night mature audience only game and a Sunday open format game.
Anyone who wants to participate reads the rules, fills out the application form and submits a photo of their cosplay. Players are selected by my co-coordinator and assigned board positions.
All players are required to attend a pre-game meeting for both safety (themselves and the audience) and to get them organized. Anyone chosen as an alternate for the Saturday game is automatically in the Sunday game if they wish.
As for Chess Masters, Since the first game is scripted (it's based on a famous historical chess match) the Chess Masters are our Kings on either side of the board and they make the moves based on the historical game. Players in this game know who they will be fighting and can plan more dramatic battles which the audience loves.
Real Chess Masters are chosen for the other two games which are real chess games. People can apply on the form to be chess masters and are chosen from the applications.
I hope that helps get cosplay chess going for KawaiiKon.
Let me know if you need help and I will get you what resources I have.
Cheers,
Kato
Public Relations Manager Sakura-con