Contrary to popular belief, I actually believe the Leafs can make the playoffs, or at the very least should be in the race right to the end with the team they have right now. That is not to say they do not need to make some moves as they clearly do, but they are much closer to being a playoff team than a lot of people are giving them credit for.
Firstly, let us not be blinded by the past two seasons of utter failure (and yes I am aware it's actually five seasons of failure but I digress). One stat that tells the tale of why they were so bad is that for the past two seasons: The Leafs ranked LAST in the NHL in save percentage. LAST. Not 20th, not 25th, but LAST. That problem is solved as far as I'm concerned as Vesa "Swiss Cheese" Toskala was shipped out of town. Even in a worst case scenario, The Monster and Giguere should be able to crack the top 20 in that statistic which I think alone brings us up the standings by a minimum of 8-10 points.
Secondly, the addition of Dion Phaneuf further solidifies a very formidable defence corps that got off to a horrific start with new guys trying to do way too much (Beauchemin and Komisarek) and of course not helped by awful goaltending. Komisarek finally had the surgery he needed and should come back healed both physically and mentally and with less pressure to carry the backend with the huge addition of Dion Phaneuf (who is to be named captain at some point this summer).
Thirdly, I feel the Leafs will have plenty of cap space to go and acquire two first line forwards (yes, first line is required because as good as Kulemin and Bozak are, they are not ready for first line NHL duty, not on a playoff team anyways).
According to Capgeeks.com, the Leafs currently have $51 million tied up in 17 players. By sending Finger to the minors that frees up $3.5 million in additional space. Assuming the cap is $58 million next season (I've heard various reports of it being $57 and $59 million so lets cut it down the middle) that would leave the Leafs with $47.5 million tied up in 16 players. Lets assume Kulemin is resigned for $2.5 million, that would put the Leafs at $50 million.
With $8 million in cap space we would need to sign five more guys. In order to acquire some top end talent, Brian Burke would need more space to work with. So the natural move would be to deal Kaberle for either a first line center (Jeff Carter perhaps?) OR a first line winger (Bobby Ryan hopefully or possibly Sharpe or Versteeg from the Hawks, potentially Frolov). And finally, Burke could acquire a Colby Armstrong type player to add some size and grit to the forward lines.
If the Leafs lineup looked as I will write below (once again wishful thinking but with Burke at the helm, a definite possibility), I'd say they'd be primed to not only make the playoffs, but perhaps pull off a Habs-style first round upset?
FIRST LINE: Sharpe-Carter-Kessel
SECOND LINE: Grabovski-Bozak-Kulemin
THIRD LINE: Stalberg-Kadri-Armstrong
FOURTH LINE: Sjostrom-Primeau(or someone similar)-Orr
Gunnarson-Van Ryn(or someone similar)
Goaltending: The Monster, Giguere