I would think you are correct about 2-3 of Hall (doubt he gets moved but i wish he would to the Leafs!) Ted Nugent-Hopkins, Eberle and Yak being gone by puck drop next October and for Oil fans sake, they better be because it means upgrading the Defense.
The Leafs have super scout, super eye for talent, Mark Hunter in charge of scouting so no doubt they will draft well from now on just as they have the last few years, look to the Marlies amazing season thus far for proof of that, of course many good trades and signings have helped them as well but it is nice to see some good young home grown talent again in blue and white down on the farm and at the big league level. Also there is the expectation that the very talented russian defenseman Nikita Zaitsev will be coming over next season and that helps the Leafs fill one spot on D that they deperately need. Time will tell how good the kid can be but he is expected to be the real deal.
If the Leafs can get one of Auston Matthews or one of the two big swedish wingers expected to go 2nd and 3rd in the draft, and are able to sign Stamkos, look out, the rebuild just excelerated ten fold. Imagine one of the top three pics plus Stamkos, a full year of Nylander and Marner, Hyman, plus getting back healthy players lost to end the season, the russian dman mentioned above and a couple free agent signings, the Leafs will be a playoff team next season in all likelihood, and most of that will happen, maybe not Stamkos but then again, MAYBE! Meanwhile Montreal's season depends on a healthy Carey Price.
The Oilers should get between first and third pick, I really hope they trade their pick and try and get some good defense, throw in Hall and Hopkins ( reason I like Eberle is that when there was talk of Hall, Hopkins or Eberle being traded he was the only one to say he wanted to stay ). Management says between the three two will be gone. Yak should also be off the roster when the puck drops next season.
Next year the Leafs should be a far better team if they draft smart and they have enough early picks.