The more I see, the more my read is that Dundon absolutely wants to be involved, but wants to stay on the right side of the line between "involved" and "meddling".
He's not a hockey guy. Period. So to consider how he conforms to any preconceived notions about the way things work in the hockey world is misguided. He's a businessman and he's bringing a businesslike style to running the team (incidentally, the fact that Waddell is also a businessman is probably the #1 reason why he got Dundon's ear). Time will tell whether it works.
But over the years, I've learned that the teachers and bosses that get the best from you have a habit of challenging you. It's not to make you feel overly uncomfortable or to say that you don't know what you're doing; if that's how it comes across, they're doing it wrong. If he's bringing that approach to a business he doesn't know, then we're screwed. But if they make you defend your idea by saying something like, "tell me why you think this is best," listening thoughtfully to the answer, and having a conversation about it, then it can work very well. The more I learn about it, the more I think this is the approach Dundon is trying to take.
As for Roddy's "we know how every coach's story ends" comment, he's just speaking to the fact that most coaching tenures end with a thud. That comment surprised me because it was more blunt than you normally see in this league, but I really can't find anything else to read into there.