Gregory's Server@arrrg great question. I feel like once you get past a few hundred all bets are off. The only experience I've had that comes close is at small startups. One of those was abt 100 people, all somewhat like-minded... even then there were plenty of squabbles over product design, goals of the company, who's in charge, etc etc. A slightly bigger startup that had great leaders was also pretty good. I think the expectation of power over others (and huge profits) is what ruins it.
@arrrg @Radical_EgoCom Just thought of the Black Panthers -- that was (is?) a group much larger than 100, and I think it was pretty hierarchical but I bet there are some clear lessons on this topic within those archives.