gokeefe-
Item 2- Greed, perhaps, but most likely not primarily for money. Perhaps, more, it was greed for control. A later examination follows.
Item 3- Inexperience? Hardly. Fink the Elder brought decades of PRR/PC experience to to Guilford. Unfortunately much of that experience focused on reducing service, not increasing it. Read or re-read the Fred W. Frailey article in "Trains" in which he discussed The Elder's earlier tenure as a division superintendent and his control of those underneath him. He, in turn, was controlled by equally demanding vice-presidents. As a principal in Guilford and one in whom the other principals held confidence, he emerged as someone who had no signicant check over how he wanted to run the enterprise. His reduction-of-services frame of reference got free rein. If problems did happen, think three disparate references -- John Wayne, Mel Brooks, and Shakespeare.
Approximate quotes:
"Never apologize. It's a sign of weakness." -John Wayne
"It's good to be the king." -Mel Brooks
There are too many potential Shakespeare possibilities, but just think how kings or princes --or principals -- get changed by their attempts to acquire and maintain power. A driven, driving, dominant, and dominating personality left unchecked can lead who knows where.
Somewhere in the previous paragraph is possibly a response to Item 1, as well.
"A gray crossover is definitely not company transportation."