Haven't seen MLB Now yet, but Clubhouse Confidential was great and I like Kenny. I think he's pretty knowledgeable sabermetricly, certainly relative to most of the other talking heads on the network, but still has to explain, and dumb it down a bit, for the layman.
When Kenny talks you can tell he knows what's going on with players the way we know what's going on with players, i.e. I suspect he plays fantasy baseball, as opposed to the ex-player commentators who feel more like they only know the star players and think everyone is really good and gonna bounce back just because they were once good, even though there's no statistical basis to expect that. It also feels like a lot of the player commentators are "fed" their opinions before the show. In other words, ironically, the ex-players feel like a casual fan talking while Kenny sounds more like one of us.