Sure. This is how I think all played out:
Replacing Monahan by Dach = Gamble
Two things here: When KH re-signed Monahan Summer 2023, he promised him to trade him during last season to a place with his consent. There never was a plan where Monahan would stay for certain. Now we dont know if MTL made an offer to Monahan Summer 2024 - which they very much have tried. Second, they didn't replace Monahan by Dach... in fact last season Dach started the season while we had Monahan too. In an ideal world, they would have prefer to have both. The mistake that was made by KH is to hang on to Dvorak/Armia over the summer and not look for a better veterant/leadership option.
Replacing Harris and Kovacevik by Hutson, Barron, Struble and Xhekaj = Gamble
There is no world in which making room for Hutson over Harris or Kovasevich is a bad thing. Now, when you look at the other LD: Harris vs Xhekaj vs Struble.... You can't affirm that Harris would fair better then the other two right now has he'ss barely an nhl D (he's not even playing all the game in CLB). So it's an easy choice: you take the intangible of both Xhakaj and Struble before Harris. Now Barron vs Kova: this is not a gamble, is mismanagement. Barron should have been traded 12 months ago.... This would have left a spot open for Kova.
Giving Montambault and Primeau the goaltending = Gamble
If there is a place where there was no way to expect the massive set back the players would have is in net. If anything, last season proved that these two could handle the pressure performance level needed by this team. I don't think anyone expected them to turn into Roy in his prime, but if they played equally as good as last season, we may not have so many blowout games.
Keeping the same coaching staff and not hiring an experience assistant coach = Gamble
Again, there is no gamble here. Last season, MTL got the all time record for game lost by 1 goal. Why would anyone think that the team was not heading in the right direction? Yeah the PP and PK where bad, but that got fix to some extend this season. So while I agree that an experience coach is needed it was also correct to expect that without any other changes in the coaching, and simply adding two key offensive players in Dach and Laine.... you may get a few more wins??
Bottom line here is that unlike a gamble, which is just hoping for the best with little effort, rational decisions where made based on info available at the time but not all of them turn out to be good. Heck... what was the mood in September? "Can this team surprise and actually make the playoff??" you dont have these kind of convo if you dont think you are building on something solid.