No question at all: Chairman's Award.
Winning the Regional Championship is a testament to your teamwork with other teams and your ability to design a "winning machine".
Putting things into perspective: it is partially dependent on others, partially based on luck, partially based on the design process (which may not have been 100% done by students on the team), and partially the skill of your drive team. That being said, obtaining the regional championship is no small feat, but not all in your control, either.
Winning the Regional Chairman's award is a testament to your team's ability to inspire others to recognize, understand, and strive towards FIRST's goal of creating more "tech-savvy" problem solvers.
Putting things into perspective once again: It is partially dependent on your team's ability to share these principles in your local communities, partially dependent on how well you communicate them within your team, partially dependent on how FIRST has inspired your team to "go beyond" -- outside of the competition.
With Chairman's, unlike Champions, the variables here are all on you -- not other teams, not a handful of robot designers, not a handful of drivers.
Now I'm not trying to belittle the importance of being a regional champion, but to me there is much more to a "Hey, look at what we have done as a team" feeling over a "Hey, look at what we did out on the field just now!" feeling.
Winning regional Champions would be great -- and an instant gratification -- but, in my eyes, winning Chairman's is much more deep-seeded and meaningful.
And besides -- there are three Regional Champions -- there's only one Regional Chairman.
