Here is some ideas, how about a 2nd rounder for Chris Neil since we need a tough guy and he can also put the puck in the net and how about AK and a prospect for Dustin Penner.
I think the only way the Habs truly get to "the next level" is to get bigger. It is great having some smaller skilled guys, but this is not the early 80's any longer(unfortunately, that was some great hockey)) and a small team like they have is not going to cut it.
Teams like Philly and Boston will run them over... I'm not sure there is one player out there that makes them significantly better, or better to the point they are in the upper echelon of the league.
I think though, your proposed deals make some sense. Neil would definitely help. I think you might be a little light on what it will take to get Penner, but you're on the right track.
This is going to sound stupid, but I think this team has to be completely re-shaped. Move out whatever vetran contracts you can,( Gomez is IMO almost unmoveable, with his contract, I like Cammi & Gionta) They have drafted terrible over the past 25 years, and haven't really had a marquee guy since back in the early 90's.(Roy)
A guy like Rick Nash comes to mind. A big guy who can score, and is still young is what this team needs. It would take alot to aquire him, and he is the type who needs a supporting cast, but he would be a guy I would be targeting if I were the Habs..................