Most teams are near the cap, there are only a few good teams that aren't pretty close. The habs are wasting a lot of their cap... Bergevin saved cap for years and was blasted for it, then he spent a bunch of it well, and was praised, now he's spent a bunch of it badly.
The big change needed is that the team needs someone with vision who can plan and build a team. Bergevin does not have those skills, but he might, with someone vetoing his dumber moves, be able to implement a plan for someone who does.
Molson obviously does not have those skills. He also lacks the desire and ability to find someone who does. We have to hope that he sort of randomly hires someone who turns out to be excellent.
The team has tried to avoid a rebuild for 25 years. They could easily have avoided it by not dumping good players for bad players with lower salaries, but that ship sailed in the '90s. They've bounced between the low end of mediocre and the high end of mediocre, but they have never been true contenders. The cup run was great, lots of fun, but it took a huge team effort, Weber's and Price's health, and a lot of luck to get there. Key injuries, a suspension, the national media calling out Chris Lee... It's not something that will happen every year if they "make the playoffs and see what happens."
The only way to make the team good is to get as many good picks as possible over consecutive years until the team is truly stocked. Once the team is good you can roll. If the team is good non-key players put up good stats and look good so you can trade them for younger guys. Try to avoid letting key guys go unless you get a key player back, ideally same age or younger. Don't sweat the secondary players. Instead of paying to retain 3rd liners pay key guys who will make worse secondary players perform better. The first step is a hard tank over multiple years, though, and without doing it like Buffalo or Edmonton, though Edmonton may have finally turned a corner. The key is to figure out who is driving a line, and Montreal is not good at it, even on their own team.
I'm just glad Molson hasn't made big changes yet. Let the team fail and aim for 2025 or 2026.