Dear Galewind and others with same issue,
Let me say first that I understand your frustration and your desire to produce an excellent award. From what I hear of your team, you have done many amazing things.
However, let me recommend a new idea:
This is the competition season - after your next regional (if you have one), or if you don't you can do this now - sit down and re-read your Chairman's award critically. Present it to a member of the community, or someone who isn't that familiar with the award.
Send the award to individuals whos' teams have experience with the Chairman's award and have earned one. Send a polite email asking for them to read it for you, and ask for what you want them to look for.
I volunteer my time immediately to give you feedback should you ever want it, and I am sure there are other people who will happily read it for you as well.
I wish you the best of luck, and just remember that many of these judges are just like the members of your community - they have other jobs and other commitments, but what all of these people give you is valuable.
Just don't be afraid to ask. However, just as Robomom said very eloquently, all of these people are busy, and that is why I recommend other community members rather than judges who have already looked at your material.