Monahan should be one of the highly sought asset amongst contenders at TDL; Habs can reasonably hope to fetch at least a (late) 1st round pick as it stands. If possible, the Habs should accept a forward cap dump in the Monahan trade to further optimize his value.
Pearson could be intriguing asset at TDL as well as it stands, could maybe fetch a (late) 2nd round pick, provided however the Habs use a salary retention on him (either their own last remaining spot or by renting one from another team for a 4th round pick). Again, if possible, the Habs should accept a forward cap dump in the Pearson trade to further optimize his value.
With Dach out, Monahan traded at TDL and Reinbacher in Europe, Dvorak and Savard would both require a significant package to be moved this year rather than next (off)season, when they’ll both become expiring UFA and easier to trade. Unless a (late) 1st is involved and the Habs don’t have to pay more than a 3rd for renting a salary retention spot over 2 years, it’d be optimal to wait until 2024-2025 before putting them on the market.
With many years left, Anderson would have to be traded in the offseason, without retention. A team would have to give a very good ELC/RFA player + 2nd to avoid giving up a 1st round pick + prospect.