I blame the nostalgic dinosaurs here (the Tremblays, Bergeron for example) who kept gushing over how Glorious les Canadiens were... but what they failed to mention/analyze is that most of the "24 Cups" were won during a time where the sport was still just a regional/backyard" sport... I mean, 6 teams for a long time... then eventually 12 teams... mostly just canadian players (very small country in terms of population, even today Canada is only the 37th most populated country, same pop as Tokyo). The city of Ottawa won 11 of the first 35 Cups awarded so they could have won a bunch more (and maybe take some from Montreal) if they didn't lose their team in 1934... The difference is you almost never hear about this "past glory".
So all this nostalgia of when the NHL was in a very different reality from today created unrealistic expectations for this team. I think new generations (people below 30-35 y/o) are a bit more reasonnable since they realize that they haven't witnessed any of this "glory" during their own life. They kinda understand that the Canadiens are just "another NHL team" like the others. Now that whole world is sending its talent over and the americans are taking the sport seriously, it's a very different story.
It's probably because of that "pompous" and entitled attitude that I have never been a Habs fan despite living here. As soon as I arrived from Europe in 1991 (never even heard the word hockey before lol but loved it right away) I was a Nordiques fan and then eventually became a Sens fans after they lost their team. Never could become a Habs fans even I tried hard in 2004 going to playoffs games.