The big question with Hutson is how he will do in the playoffs. He has overcome every obstacle so far, and he is playing well, but in a seven game series other teams may be able to wear him down and he is not going wear down other players.
Most of Hughes' acquisitions have a visible point, a nice contrast to some recent GMs who seemed to view trades in terms of value in and value out. It doesn't matter if you win all your trades if you only ever trade for scoring left wingers and you end up with twelve of them. Taking Slaf was pretty clearly aimed at getting some size in the forward group, Wright, Caufield Suzuki, and Gallagher, plus possibly Mesar and Roy, makes a pretty small group. Dach was a stab at a big second line center for the same reason. Newhook is less clear, but they are short on speed, so that could be it.
It's not so much that the habs can't succeed with Caufield and Hutson playing regularly, it is that they will have to balance them with others who are more physical and who can occupy more than one opposing player to counterbalance the opposition being able to push Montreal's little guys around. The rest of the team will always have to play a little harder on D to compensate.
They will need Guhle to put on some muscle and play more physically and Xhekaj to impose himself with hits more than fists. They already need to get some more righties, and they are going to need more big defensive specialists and fewer offensive guys. Quite the change from when they had mostly big guys on D who didn't handle the puck really well just a few years back. They are so lacking in defensive D that they can't afford to sit Savard. That's a major weakness.