The Canadiens were stuck in mediocrity for the longest time. Yes there were seasons where they were a little better and seasons where they were a little worse, but they were basically just "there". They somehow managed a Cinderella run through to the Stanley Cup finals but it was clear they needed a rebuild. Nobody thought the fans could tolerate a real rebuild (management didn't even want to use the word in public), but they decided to do one (no choice) and low and behold, the fans actually accepted it without much of a complaint. The arena is packed every night. They're in year 3 of their rebuild and still nowhere close to being a "good" team, but some of the pieces are there, and the fans see glimpses of what the team can potentially look like in a few seasons. Just like the Flames, they have some long term contracts they're trying to get rid of (clean up) from the last management team, but they're getting there.
All this to say that there's actually no worse place to be then a middling team that's just "there". Hope the teams rebuilds (at least somewhat) even though there's no guarantee it will end up working.
Yeah its the same thing in Toronto post lockout, except our "run" was a 7 game series vs Boston lmao.
It probably comes from all sides;
Owners think fans will stop supporting the team
GM has an incentive to keep his job and thus act like "it's all going according to plan, just 2(0) more seasons and we'll get there"
Coach and players doing the best they can and don't want to state the obvious for "not being a team player" by pointing out they can't possibly win with the personnel there
Winnipeg is going through the same thing, ironically the teams are so meh that if you merged these middling teams (Winnipeg+Calgary and Toronto and Montreal when they were mediocre), they probably still aren't even a cup contender.
Personally I'd rather a tedious rebuild than a tedious mediocrity because that can always be followed by the tedious rebuild anyways.