I got a response from the email I sent to the coordinators with the questions I had (to which she answered very promptly). I hope some of your questions are answered by this as well. This is the reply I got:
We always look forward to new people visiting the chili cookoff.
There are currently 22 cookoff teams registered with a possibility of a couple more registering the morning of the cookoff. There is a large crowd of spectators. Last year we estimated over 2,000 people attended. While there is no entry fee to the grounds, tasting cups are 4 for $2. Fresh sample cups are to be used to sample each chili. (We are raising money for charity.). Your children are always welcome too. This is a family event and there are activities for everyone. Be warned though that some of the chili can be pretty spicy.