I think the thing that's frustrating above all else is that this team has been shit at player development for so long, but don't seem to ever recognize that and try to sell high on guys they don't like for whatever reason. If they're going to suck at development at least they could start trading the prospects before they've lost all their value.
Like yeah, turning Kotkaniemi and Galchenyuk into Dvorak and Anderson is good asset management relative to what those players were worth at the time they left the Canadiens, but it's shit asset management relative to what you could have got if you made an actual bold decision and just moved the guy that you irrationally hate and will never give a proper chance.
Same with Domi. They knew he was a poor defender and he struggles on the wing where he doesn't have the space to distribute. Instead of recognizing that those flaws would make him unsuitable (or at least would make the coaching staff perceive him to be) for the system the Canadiens wanted to play, and trading him at peak value after a 72 point season, they hung on to him, put him on the 3rd line as a winger, and pissed him off on the 4th line in the playoffs for the sake of a guy they ended up trading for Dvorak 15 months later! I will never understand why they have these players they hate for being too small or bad defenders or whatever but they just hang on to them as if Max Domi is ever going to start defending like Phil Danault instead of just cashing in at max value.