If HuGo added a bit more talent over summer I'd agree with you in that it was a perfectly sensible gamble. But the fact that he decided against injecting other NHL talent really puts the same kind of pressure on Newhook (and on a worse team that can insulate him less) so it seems like Newhook is facing the same circumstance as he had in Colorado: the need to produce in a 2nd line role. He had a pretty bad time in the last playoffs too, 1pt in 7gp.
He's young and will still develop of course but if last year's demands were too much for him then I don't see how this year's demands will be perfectly suited to help him grow. A lot relies on (1) MSL's "magic" and (2) Newhook's personal and internal growth, fresh start, etc.
One thing that does bug me is the tendency to acquire physically flawed players -- be it bad skaters or undersized ones -- and then have to accommodate other acquisitions and decisions in order to make up for that. Now we have too many small-ish forwards in the NHL and too many small-ish forwards in our prospect pool. Owing to this fact, I can't help but feel the Newhook acquisition has to be a slamdunk success in order to justify itself. If he tops out as a 50ish point, nimble but non-physical winger we've basically swapped Drouin for Newhook at half the cap-hit -- not bad, good depth, good NHL asset (bad trade asset owing to playoff reputation, much like Drouin and Tatar) but it won't move the needle.
Wanted to address the bolded points above, because I don't think their entirely fair.
The first one, I agree that Newhook still does have the pressure to produce. It's going to be his third full season in the NHL after 2 underwhelming ones with Colorado. But I think the biggest difference is that unlike Colorado, the Habs are not a Stanley Cup contending team, meaning that even if he makes mistakes in the top 6, he will have a bigger leash and would still stay in the top 6. Just by being in that different environment will remove *some* pressure from him and the goal is that he can hopefully thrive in that change of environment.
tldr; he'll still have pressure to produce, but will have less pressure to produce right away.
For the second one, what do you mean by "acquire" is that only through trade or do you also count drafted prospects? Unless I'm forgetting someone, but all of Barron, Matheson, Newhook, Monahan and Dach are all good skaters and only Newhook is the undersized player here.
I actually don't remember any acquisitions or drafted prospects that were physically flawed prospects. If you're talking about the likes of Roy, Farrell and Mesar, only Mesar was drafted by Hughes. I'd actually argue that most prospects drafted by Hughes are big boys who can skate, so that argument doesn't really work here (Slaf, Reinbacher, Florian, Engstrom, etc.)