The complete rebuild is three yrs away, unless they get really lucky.
Maybe the Leafs will be like Boston and move the few assets they have left at the TDL?
The Leafs have to get younger. This core is struggling and probably won't take you any further than it already has. That's not definite, but it's the way to lay the odds.
In their situation you consider moving core guys in order to restock the farm and set up for future runs. These can be very unpopular moves for the fanbase and owners, but we have literally seen what only doing the popular thing does for the Leafs franchise.
If Treliving manages to do the unpopular hard thing and break up the boy's club and bring in some younger, hungrier guys that no one's heard of yet I'll be favorably impressed, even if it doesn't work out immediately.
Fundamentally that's what Boston did with the Joe Thornton trade, and that combined with drafting guys like Bergeron, MacAvoy, Marchand and Pastrnak (in other words, not wasting picks and drafting well) was what gave them that long run at contending for Cups.
It took a few years, but building from the waiver wire with unknown guys, keeping the guys that work, dealing the guys who didn't fit the vision while they have redeeming value (examples: Tyler Seguin and Blake Wheeler), and developing a consistent culture based on defensive responsibility and hard nosed hard hitting hockey with guys like Chara, Boychuk, McAvoy Thornton, Campbell, Ference, etc, was what gave them the chance to make these runs in the first place.