Gee, I don't know why Florida would trade the superior Montour, who is cheaper and has term.
Armia is long term cap liability in a cap flat league. Hoffman is way too expensive for his additional two full years for teams to take on.

I can't get past the first trade. That is not a good return. ​
Monahan is worth next to nothing to the Habs.
They aren't trading Dvorak, especially at a loss, one season into giving up a 1st and 2nd for him.
A 1st and 2nd is a mediocre return for Toffoli. I'd keep him unless one of those picks were a good C or RD prospect.

Calgary - maybe Toffoli for a second. Doubt they'd give up a first (prior years' lessons). MTL Keep's Dvorak, Calgary keeps a 'better-of-late' Monahan. However Calgary needs to trade Monahan's salary at some point to sign their pending RFAs.

Hoffmans 0% interest in playing defense already makes him hard enough to move. You add in the 33 34 year old years. Good luck.

1st Trade - Monahan doesn't have any value to Montreal. He's trending downward and the Habs aren't looking to compete short term.

2nd Trade - Montreal rejects, Hoffman shouldn't be traded while his value is low. Might as well keep him and see what he is.

3rd Trade - Chiarot doesn't have to be worth a 1st, that's what he is going to get. Value isn't even close here for Montreal.

4th Trade - Value isn't close here for Lehkonen, he's getting at least a 2nd, and then you're probably still going to have to outbid that to get him from other teams.

5th Trade - Any value for Armia is a win. I don't see any team actually giving us value for him.

6th Trade - I can see Kulak getting more than a 6th, likely a 4th.

Montour > Chiarot, easy decline

This is not an accurate description of Monahan. He hit his all time low and has been trending back up as of recently. If anything you should view this as a full refund on the Dvorak trade (which you aren't going to get for him anymore) and then swapping Toffoli for Monahan. SM can still very likely return at least a 1st next deadline