MOE's 2007 Chairman's Award is posted at the link below. (It obviously worked well!) We also had large posters that the students used when presenting to the judges, highlighting some of our programs and statistics. We found this was easier than a Powerpoint presentation or handouts. In the pit area we had our yearbook and samples of the books from our reading program. Don't forget that the Chairman judges do come around and talk to the students at the pit - be prepared.
the main problem we had in writing the essay and summary was getting it down to the correct number of words. The bullet point format worked well as well as liberal use of abbreviations.
http://www.chiefdelphi.com/media/papers/1983