Well, under Hunter Toronto has completely replenished their pipeline. It also helps that most teams in the division have had serious poor runs that have helped replenish their systems. That said, the team's general love affair with character and fitness isn't helping them.
Leafs drafting was poor for many years so they made some changes and it's yielded better results.
Bruins didn't draft well for years either. Their hopes are with their last few drafts.
Tampa had 5 players on the Canadian world junior team and only one was a first rounder (Brett Howden 2016 27th).
Sens drafted very well for several years, finding good prospects all over the draft.
Florida has a nice young core, definitely built with high picks but their prospects beyond that were rated well above the Habs (5th in the league).
Similar for the Sabres (ranked 7th)
Wings have been drafting later for many years but still come up with good prospects.
The Habs need a couple of good drafts soon in my opinion or they risk falling behind in the division at some point.