Patrick,
Based on your descriptions of Pine Valley, isn't that an instance where the "dictator prinzip" failed? You have repeatedly talked about the deterioration of the place because of tree encroachment, and others have mentioned other areas that have gone down. Others, like Tom Doak, have talked about how Augusta has been changed materially, and not for the better - again by a dictator. Riviera also belongs on the list, and many of us know what happened at The Creek Club (where boodles of Raynor bunkers were removed, among other things, again by a dictator). We could probably add Yale to the list where an individual (there the superintendent years and years ago) with all power harmed, or even desecrated, a great golf course.
Of course the counterargument to this would be that a committee would have been even worse, but I'm not so sure. The more people involved in a decision, the less likely it is that anything will happen. That can be a good thing when one favors preservation of what is there (not so good when you need to restore what has been mushed).
I'm not decrying the dictatorship, just thinking that it isn't the be-all and end-all, and that each management model has pluses and minuses. In the end, I think it depends more on the character of the individuals involved than the model.