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.
As for the cost paid, those are fun picks to hold and interesting prospects are found at those spots but they often don't amount to much -- it's not something worth worrying about at this time. Hughes paid the price he thought was fair for the player. We'll know soon enough if Hughes is generally a good at asset management or not. Personally I would've liked to see Hughes make some home-run swings for the best ranked C prospects out there with both those picks. Our prospect C depth is awful and we need some bets. But that's aside. Newhook, if he pays off, will be worth a lot more than those two picks.
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.