No offense, but these are silly (albeit sincere I'm sure) statements.
Football, particularly Bills football, might be a passion of the fans.
But believe me, it is a business first and foremost to owners, FO people, coaches, players and everyone else associated with the NFL as their profession.
Do you seriously expect someone like Mr. Wilson to do something crazy like sell the team to Kelly on the cheap just because he thinks Kelly will keep the team in the area? He didn't get to where he is by being a bad businessman.
And the answer to your "How much money do you need to leave your family?" question is "as much as possible".