This isn't NHL 15, you can't just hit the "reset button" and trade virtually everyone on this team, sorry but it doesn't work that way. In this day and age with the cap and many teams near or at it, it becomes a lot more complex.
Lets get real here as great as Kessel is for example he's making too much $$$ for teams to take that on long term, odds of him being traded are slim to nil given were still in a playoff spot. Now if somehow we are officially out of it, sure you could trade him but the amount of teams looking for a skilled one way winger isn't that many and even then you won't get a kings ransom in return for him either.
The most realistic thing is things need to change at the top, what I mean is the mandate shouldn't just be "make the playoffs", it's incredibly short sighted and we're giving up too many assets in a deseperate attempt to get there, not to mention spending right up to the cap limit. Realisticly, the manadate needs to change, its' all fine and dandy to shoot for the playoffs but there has to be a long term vision for this team, one that includes more then simply "making the playoffs" on a year by year basis.
Shanahan was a smart call, I admire the signing and so far he's preached patience which is a thing that the Leafs have no true concept of, I think slowly that approach is beginning to change. What needs to happen next is he needs to fire Nonis and Carlyle, these guys just aren't he;ping the team and havent been for ages... any fool can see that. As for who coaches? I think managment needs to find a coach that wants to play the style THEY envision, right now its a puck possession team, fair enough but Randy is the 100% opposite of that, fire him.. they really shouldnt be waiting around for Babcock to become available its' arrogant and foolish assumptions by doing that, hire a coach that believes strongly in puck possession and hire him as an interim, if Babcock suddenly becomes available in the fofseason then open discussions with him.
Next up, they need to unload a few players to clear up cap space going forward and bring back draft picks that are sorely lacking. Who are those players? Lupul, Franson, Bozak, Reimer.... all 4 of them need to go! That right there next year frees up 11 million in cap space and nets us several draft picks we can use at this years draft...
As for free agency, stay as far away from that mess as possible, all those players are overpaid and really not a smart idea to blow money that way. As for the players that should be resigned? Bernier, Kadri, Santo, Winnik (as long as his demands are reasonable).
Drafting? We still have a bad need for skill in this organziation, use the 1st rounder to draft another stud, bury him in the minors next year and don't call him up for a year... time to be paitnet with our prospects, let them learn and grow instead of rushing them up