As a Canes fan, I think the Leafs are going to surprise a lot of teams and be better sooner, rather than later. They have a great FO, a great coach, good player personnel evaluation, a good prospect pool, lots of picks and gobs of cash. You can see how much more structure and effort is in their play, even with a line-up that lacks talent.
IMO, the problem in the past has always been a dysfunctional management and no vision and long term plan. That's in place now and when they do turn the corner, they'll be good for a long time. The biggest weak spot is D. Rielly is a really good cornerstone and even Gardiner can be a piece of it, and Dermott cold pan out, but they really need to beef that up. Rather than trying to trade for big names and/or signing them in UFA, IMO the next two drafts can go a long way to address that. Sign a couple of lower tier vets as stop gaps that can also act as mentors to these guys kinda like Carolina has done with Hainsey and Liles to go along with Faulk, Hanifin, Slavin and Pesce.