All I've said is that they will reach the finals this season, because the East doesn't have an appreciably better team. The West is a different story. Vegas and Colorado are different animals, and whether the Leafs could beat either of those teams in a 7 game series is a different conversation (and obviously depends on whether either of those teams comes out of the West). I had originally thought that Jersey would be Toronto's biggest competition in the East, and while that still may end up being the case, Jersey has dug themselves a bit of a hole, and they need to find a starting goalie even more than the Leafs do (there is no Woll waiting to come back in Jersey).
In the end, I think Colorado should win the Cup, but it requires them to replace RJ with a better centre option by the deadline, and it requires Landeskog coming back for the playoffs. If those things happen, I think Colorado will be hard to beat. In the meantime, I do think the Leafs will eventually pass Florida and Boston. I also don't think it will be some grand achievement when they do it.