With Cherry you have to figure part of it is an act. There is a reason he wears ridiculous suits and his segment intro is filled with clips of himself doing random and silly things with very little hockey laced through it. People don't tune into coach's corner to watch Grapes spout off about numbers and charts, they want him to showcase some big checks, a human interest story involving dogs/military/children with disabilities, talk up some good old Canadian boys doing our country proud, say something mildly offensive about players from another nationality all while arguing and undermining Ron Wilson at every opportunity. How vocal the duo can be about managing their segment time and constantly failing to be on the same page as their graphics staff when cutting away to clips is amateur hour at it's worst but it keeps happening because we love it. Then there is the constant speeches towards the "kids" in the audience that will become the future of the league (but only if they eat their vegetables and do everything Mr. Cherry says). Do kids watch through the intermissions? Do they look to advice from an old guy in a silly suit? Probably not but it's not for them, it's for us. It's part of the charm of the show. We aren't supposed to take things too seriously or gain any insight from watching, though it also allows Cherry to throw a few actual barbs at some players/coaches/etc. that deserve it (like Kane earlier this year) and get a pass for attacking player's character because this old man has been yelling at kids to get off his lawn for years and it's too late to change him now.
At the end of the day though, Cherry is very likely more old school than many of the successful decision makers in the league but he's also a lot more knowledgeable than he let's on. You don't play and coach in the NHL and spend this much time involved in league media without learning something along the way.
(unless your name is Mike Millbury)