In hindsight, sure. At the time, I was fine with it.
Exactly. Hockey, and life, are more like backgammon than chess.
In backgammon you choose a strategy, revise depending on your dice rolls, and adapt. Even the best player will lose some games, though not many, to a lucky lesser player.
In chess there is no element of randomness. If you play a perfect game you should at least get a draw. A good player may draw with a less good player, but losses at high levels are rare. Rarer still for non-human opponents.
In hockey it is not just hard to tell if a move is good at the time it is made, it can be hard to tell for several years after. The trade looked good before Dach got hurt, and before it became clear that most of the D in the habs system did not actually make Romanov redundant. If Romanov gets hurt, or Dach gets healthy views could change again.
Most of Hughes' moves depend on young players developing one way or another. He can take good gambles or bad gambles, but if he only makes sure bets, or even quite sure bets, he will get into the "trades are hard" mode that Bergevin got into as he wanted to win every trade. Note that this is much better than Houle who wanted every trade to be even and lost them all.
I don't agree with all of Hughes' moves, but I have far less information and knowledge of hockey. I doubt Dach was his ideal target, but he provided a chance of filling a spot without paying an unacceptable price. It doesn't look like it is going to work out, but it did not cripple the rebuild. I'm not going to rant about it.
I'm iffy on Newhook. He looks good at times, but he's not really effective. He adds some speed they were missing, but he is yet another smaller non-physical forward. He has a year or two to work things out. Again, I might not agree with it, but I'm not going to lose sleep, either.
The Michkov/Reinbacher decision was polarizing, but I can understand the point. The habs have enough smaller forwards that it's tough to use a top pick on another one. Lafreniere showed the challenges of drafting when you already have the spot filled on the top 2 lines long term. I mean sure, BPA is miles better than what the habs have done for decades, "take the next big center on our list even if he'd probably be available in the third round," but BPA is very subjective. Few teams think they are taking the much worse player at whatever position, but there are still lots of busts among the top picks. BPA pretty much translates to "don't screw up" because it becomes an inspired pick if it works out. The habs picks have been more screwups than non-BPA, sure, they reached for size or position, but they did it really badly. The habs drafts often sounded really good when TSN and RDS analyzed them over the last many years, and almost none of the players worked out. The last few drafts have looked weak, and downright weird, lots of goalies, late round picks with even less chance than most late round picks, but a lot of those players are looking good.
The best GMs will have misses, and most of them will also have some costly mistakes. Overall the rebuild looks good so far, they got some good players with the high picks, the team looks competive so far. We may get to see how the team does in the playoffs. The main question is whether they were putting out max effort for their streaks in the regular season, because real contenders will have another level in the playoffs.