There are good and bad things about being in a hockey mad city, and I wonder if you are falling a bit into the bad part of it (not just you btw). You know your team better than I would, but the big issue with a pressure environment is that the memory is long. Like with the Oilers, when times were bad they were miserable because there was intense pressure to win right NOW because every year of missing the playoffs highlighted the failures of the rebuild, and it led to super aggressive actions that didn't work and bad decisions (basically all of the Chiarelli era, and before even).
The best feelings the Leafs had were when they pre-empted a season by saying they were freezing ticket prices and that the team would be bad (I think this was right after the Matthews draft). They primed the fanbase for low expectations. The pressure was vanished because the fans and media were on board. But, the team ended up over achieving.
The Leafs have been bad this year but the pressure will prevent the team from bouncing back, especially if numerious players and the coach now have the magnifying glass over them and people's jobs might be at stake in the short term.
Yes, this is concerning because it fits a pattern, either with the Leafs or with other coaches being tuned out by their teams, but it also fits the pattern that I brought up: early season zaniness. Just because there isn't a logical excuse of sucking, like the Avs for instance, doesn't mean that the reason is that the team is bad.