I wonder if the best thing to do this offseason is get an Oleksiak replacement and nothing else. The current team should be good enough to make the playoffs, so you get half the season to evaluate the youngsters and healed vets, and then know what to load up on at the TDL.
Alternatively, the team is not good enough to make the playoffs, and the TDL signals the start of a quick retool as you sell off Klingberg, Pavelski, Radulov, possibly Comeau and Sekera, and at least one of goalies for what should be an excellent haul of futures.
Either outcome I would be OK with. Mostly I just don't want to be a bubble team at the TDL that does nothing - either buy or sell, because there's too many important expiring contracts to fence-sit this time around.