I agree with everyone who says the Vets need to go especially those with expiring contracts. Even if Montreal makes the playoffs it's likely to be a 1st round exit with or without them and you may as well give that experience to the young and up and coming players if the playoffs do come to fruition.
Savard UFA - Easily replaceable as far ice time on ice is concerned - 2nd Rounder
Dvorak UFA - Might land the Habs a 4th but you take it and let Beck play
Armia and evans expiring contracts if you get a 1st for the combo you take it and if you don't get what you want hold on to them and roll the dice on new home town deals next year.
Vets with Contracts that can also get you a decent return and are replaceable.
Matheson - can prob fetch you a 2nd maybe a low end 1st once all the D have been traded and teams are moving to their 2nd and 3rd options.
Gallagher - love him but he's on the decline despite having a fine season, I would take what I could get for him now but doubt they can move that contract.
Josh Anderson has some value for a playoff team looking for depth I really think he can get a 2nd from someone or be used in package with Armia Evans. (Armia Evans Anderson for a 1st and prospect + salary dump tp make the trade work)
Newhook may fetch a 3rd or 4th to a team looking for some depth on offence. He has good wheels and has shown some promise but Montreal just isn't the right fit since they're weak at C. Might as well get rid of the cap hit.
I would try and trade for Seth Jones or Noah Dobson (highly unlikely to acquire) either at the deadline or at the draft table and if that doesn't work try and sign Chykrun as well signing Ehlers in free agency.
Obviously this leaves a ton of holes in the lineup but that's where you give the kids some experience and hope they squeak into a playoff spot.
Finish the year like this assuming no big names come in
Caufield Suzuki Salf
Roy Dach Laine
Heineman Beck Gallagher
Florian Xhekaj Kapanen Tuch
Carrier Hutson
XHekaj Strubble
Mailloux Engstrom
Reinbacher needs some time in Laval due to a injury plagued season
Montambeault
Dobes
NEXT year could like something like this:
Caufield Suzuki Slaf
Ehlers Demidov Laine
Heineman Beck Dach
Gallagher Kapanen Florian Xhekaj
One of Dobson Jones or Chykrun - Hutson
Mailloux - Ghule
Xhekaj - Engstrom
Strubble
Reinbacher needs some time in Laval due to a injury plagued season