My biggest question on offense would be is Johnny Gaudreau part of the problem or part of the solution? If Johnny is part of the problem, rip the band aid off and move him.
If Johnny is part of the solution, The Don has to do everything in his power to get him going. He can't pay a guy $9.75M to be a 60 point/-27 player for the next 5 years. He can't wait on a bunch of unproven prospects to get his superstar going. He needs to use his available capital to solve this problem now. If that means trading valuable players, picks, and or prospects, so be it.