The thing that impresses me the most about Cholowski is that he is always operating within the framework of the 5 man unit. He is economical with his own movement and positioning, and is consistently aware of where the other 4 players(usually in front of him) are on the ice.
You can see in Cholowskis game, that he recognizes that sometimes if you want to get the puck to player or area C, you have to make a simple play over to player B first, and watch the rest happen from the right position. He's always adjusting his position, and the placement of the puck to maximize the effectiveness of his 5 man unit. And as a non-technical aside, he has great body language, taking equal pride in tertiary assists and primary assists.
That kind of selflessness and birds eye view increases it's potency as the calibur of your teammates increases. And it's a great trait for development, because it makes it so his in game 'reps' so to speak, are usually productive from a technical stand point, whereas a lot of teenagers playing hockey are going to lose some shifts to the chaos.
The biggest weaknesses to his game, are his strength, his shot and his d-zone positioning. The 3 easiest things to develop post adolescence, especially when an NHL team is taking an aggresive and direct approach to your development.
I think he has a chance to be a lot better than the players he's usually compared to, and a lot better than most people imagine.