First post on the board, so bear with me here...
It's evident that this team going forward isn't going to challenge for a cup in any fallible way possible. There are certain players that are lock to stay as a "core", but there are others that are nothing but fixes or part of the quick retooling process built-in by Burke, and further reinforced by Nonis by acquiring Clarkson.
Keep: Reilly, Gardiner, Bernier, Kessel (or if we can move him for the number 1 pick next season, as McDavid is incomprehensibly talented), Van Riemsdyk, Phaneuf (Debatable), Mcclement (top 5 Pker in the league and integral to bolster the PK unit) and Bozak.
Sell/dump: Kadri, Bolland, Clarkson, Raymond, Reimer, Kulemin (although debatable as he's a solid second liner), Lupul, Gunnarson, Orr etc.
What this does is keep the "core" players (I.E the ones with growing potential still) on the team, while ridding us of the dead weight that plagues the team rather than help on a consistent basis.
At best, we're getting a 7-10 pick (depending on how many more games we lose this season). There are a plethora of solid pick-ups we can pick from there, ranging from solid centers (Ritchie, Nylander etc.) and defenseman for the future which we need.
Next season; BOMB. Adios. Sayonara! The draft after this one is the draft that changes franchises. In the same way Crosby changed the Penguins, Mcdavid can be that for us. With solid core players in the people I posted above, a growing defensive core (with potential picks at that spot and the developing Stuart Percy who should be playing with the leafs very soon) and a stud goalie with Vezina potential (with a better defensive line helping him, he's quite easily a 1.90-2.05 Gaa goalie given his credence), the leafs become primed FOR AN ACTUAL CHALLENGE.
So in hindsight: Continue to lose the rest of the season and pick up a solid first round pick this draft. Get rid of the deadweight to make the team less deep while letting players like Reilly, Gardiner and Percy develop with less pressure from the playoffs, and "tank" (hate the word) for the franchise, generational player in Mcdavid.