Not anytime soon. We need to string together a few tournament appearances before something like this could happen.
Not true. Pretty simple actually. Get one of the young up and coming Chicago rappers with ties to the players (or is a fan) to come down and do a song or two during the event. If Dee gets things back on track from whatever is going on have him act as a master of ceremonies/hype man. Keep the energy high and make it fun.
Biggest mistake is to do anything resembling a practice or scrimmage. It needs to be fan entertainment more than anything else.