For 2023-2024, I think acquiring another 1st round pick would more likely come leveraging the Habs' cap space rather than selling a player - but even then, it'd be a steep hill to climb.
As for potential targets for this strategy before the season starts, the two most obvious team would be Toronto and Pittsburgh; they must must each shed 2-3M AAV to be cap compliant.
Toronto's likeliest candidate for a cap compliancy trade appear to be Brodie (5M AAV, expiring UFA). For Pittsburgh, I guess either Carter (3.125M AAV, expiring UFA), Grandlund (5M AAV, 2 years) or Petry (6.25M AAV, 2 years).
Problem is, the Habs simply don't have room to take on a "cap dump" player on their roster like they did at the time with Monahan - and especially no room whatsoever for yet another defenseman.
Montreal's role in cap relief trades could thus be limited in the short term to "salary retainer" in a 3-way deal - and this second fiddle role usually only gets second-rate asset. Unless maybe the salary retainer's fee the Habs could leverage by retaining 50% on Grandlund/Petry for 2 years generates one. But would it be worth it?
