Say what you want about Skip, he's not a better player than SAS but he's a way better GM than SAS could hope to be.
This some Jerry West v. MJ shxt
Skip's been way better about scouting on air talent to work with him. Everyone eats with Skip. His talent and most of his diva tendencies are behind the scenes and not usually on camera (career wise).
The reason I don't think SAS and Shannon will work is because Shannon is a HOF player that is one of the most recognized on air personalities. SAS can't treat him like Max and the last person SAS worked with on his same level was Skip.
Give it time but SAS diva tendencies are going to get in the way of him and Shannon working well together.