Flight departments are like marriages, no one really knows the dynamics unless they're on the inside. I see lots of departments, the good ones are larger, more professional that way; have 15-25 pilots who have a good mix of backgrounds; a "principal" who respects the department leadership; and leadership that leads. The single plane, single crew operations tend to be run by the owner who holds the Chief Pilot by the balls--it doesn't have any standards to fall back on. There are exceptions, of course, but, for me, larger is better.
FedEx would be an example of an outstanding department. I won't name them, but some single plane operations couldn't get me for $500,000 per year.
GF