Maybe a better example of when extending guys out of ELCs isn't a slam dunk even when it should make sense is the Minnesota Wild.
With Matthew Boldy, they extend him 7/49 during his last ELC year. Cool, Matt Boldy is awesome at hockey. Great contract. Except...
The Wild are in cap hell from the Suter/Parise buyouts. Instead of paying him $7M AAV right now, they could have him on a 2/7 bridge. The Wild are also 12-3-3, have Kaprizov scoring nearly 2 PPG and a surefire MVP candidate, and probably the best goalie in the league this year.
They could have $4M more space to play with right now for a team that suddenly has a lot of ingredients to make a real run. Maybe that would help. Maybe not. But we won't know because of that Boldy deal capping them out when it didn't have to.