Tough to 'know' anything. But he was under Coach Brown (tremendous coach) and has huge respect around the league to where people were talking about him as a GM candidate with no experience at all . He has at least had some coaching experience.
Completely different types of players. The grinders tend to be much better at being a head coach. Doc Rivers comes to mind. The super talented like Magic? Then Clyde Drexler's turn at his alma mater comes to mind.
To add on to that, I've been very impressed with him when I've listened to him talk about/analyze a game or player. There are those who are complete blow-hards who just talk to hear themselves talk (Steven A, Bill Walton, Charles Barkley, etc) Then there's those who on occasion can say something that is insightful, but there isn't much value in what they say (Shaq, Olshey, etc) Then there's those who can effectively communicate their basketball knowledge to others (Kenny Anderson, Jeff Van Gundy, etc). Based on the interviews and analysis I've seen - I'd put Billups as a step or two ahead of that. I'd say Magic is the same group as Shaq & Olshey. Not a great comparison for Billups IMO.