The best way to build a contender is through the draft so we'll start here.
Habs have the #3 pick, it's simple if he is available, draft Alex Galchenyuk. We need wingers on fwd more than anything but that doesn't matter Gally is a game changer, they won`t have many chances at a player like this.
Sort out the contract mess
Re-sign Price at a reasonable cost. Fleury makes 5M a yr, and is a fair comparison to model his contract over (let's hope). Regardless Price will sign long term somewhere between 5-6M.
Lock up PK as long as you can, his next contract will be his huge pay day. He didn't have the best yr and that should be used as leverage. Comparable contracts to aim for: Luke Schenn 5 yrs/ 3.6M per, Josh Gorges 6 yrs/ 3.9M per.
Eller and Emelin are two big pieces of the future. Mtl is in cap hell, it's no secret. Here's where you can leverage a lot of value and try and continue to stretch the value for your dollar with long term deals.
Both camps might be in favour of 2-3 yr deals to earn their potential value sooner than later. Try to get Eller on a 4 yr deal at 9 M, (1.75, 2.25, 2.5, 2.5) Eller will more than earn that deal and offer Emelin something similar money wise.
Time to rid some of the bad contracts. Bury Gomez in the minors, it`s the only option as he continues to get worse. I like the guy, but it`s just not even close to worth keeping that cap hit.
Try to get rid of Kaberle, find someone at the draft anything, if not buy-out. I trust St Denis way more on the ice in any game situation than Kaberle.
Recommend breaking up Cole and Pacioretty to future HC, talent needs to be distributed on the top 2 lines
Bring in an offensively skilled winger to play with Eller, I would make a play for Semin if we can rid Gomez`s contract, not enough firepower on the wings.
Give Bourque till December to prove he can produce offensively in some way, if he can`t deal him.
Try to give Gallagher a full year in the AHL unlike the Leblanc treatment, AHL was huge for PK, Pacioretty, Eller etc.
Get a decent goaltending prospect, depth is thin after Price. This will go a long way, the Bulldogs should be competitive next yr with Gallagher, Bournival, Holland, Palushaj, Dumont, Kristo, Tinordi, Beaulieu, Ellis etc.