If I became GM of the Habs...
1. Full retention TDL trade of Plekanec for a 3rd, nobody's giving up more than that for him @ essentially $1M for the final 1/3rd of the season.
2. TDL trade Pacioretty to a contender looking for scoring help (looking at Nashville). 1st + a solid prospect.
3. At the draft, trade Galchenyuk to a team like San Jose who needs a young forward with potential. Can probably get their first depending on where it is.
4. After FA opens, trade Weber for a package of Moulson+Bogosian+2nd or Lehtera+MacDonald+2nd or the like. Similar to the Phaneuf trade, it's about getting out from under that contract. Take on a couple of another team's bad contracts that add up to more than Weber's cap hit and hopefully they're willing to take him on for 8 more years...
5. Wait until the end of July, pick up some bargain vets to fill out the roster. Hope they gain some value, trade them (and Byron) at the deadline for picks, even 6th/7th rounders help.
6. After July 1st, 2019, trade Price @ 25% retained ($7.875M cap hit) to a team in need of goaltending - NYI, CGY, BUF, etc. - it doesn't matter if they're in division or not. Getting max assets and moving the contract is the biggest part of this trade. The Habs are going to suck for a couple of years, it won't matter if he's a Sabre or a Golden Knight, as long as he's not a Hab at this point, because he'll be 32 at that point, and he's a barrier to rebuilding. 1st+2nd+good prospect (or a U23 player of equivalent value)
7. Repeat the process of signing bargain vets and upping their value before dumping them at the deadline for mid-round picks.
8. Do not sign any July 1 FAs until 2020 at the earliest. I also wouldn't be looking to add impact players unless they fall into my lap before the 2020 draft either. The process is about accumulating as much young talent as possible, getting the highest picks possible, and praying it works out. If you can move out Alzner and Shaw in meantime, you jump all over that as well. The only pieces I wouldn't really be looking to move are Drouin, Gallagher and Mete, and even then, none of them are untouchable. At this point, if I was the Habs GM, I'd really just burn it to the ground.