Jessica,
I thought that Chairman's was the long-haul award, the award for the teams that do exactly what you say isn't happening--keep sustained programs alive and provide aid to the FIRST community throughout their history. You can't win the Chairman's just because of one year--you have to build to it and really show that you're keeping on.
I'll use my team as an example because I don't really know that much about other team's efforts (sorry). We spent the money that would have gone to another regional on a machine trailer for the regionals to have machine shop support, and have helped a lot of teams stay operation at competitions. We brought it last year, this year, and will continue to take it to regionals to help out.
Mentoring teams can be ephermal, you are right, though. I agree that teams should spend a real amount of time mentoring a team, not just mentoring as many as possible and adding them to the list. Last year we mentored Milpitas (1120), and two weeks ago we played them in the finals in Sacramento. That's pretty worthwhile.
You could very well be right; I haven't been around FIRST for nearly as long as you. The judges at a regional have to pick someone, and it may be true that sometimes they just pick the team with the longest list of "accomplisments." Hopefully, though, the teams that really do add to the community will be picked at their regionals, and the national judges will find the real sustainable programs for the national award.
Even still, I'd prefer a Championship.
