Goaltending is an interesting one. I like Kosko, but he needs a running mate. There's a couple good UFA options (Lehner, Holtby, Greiss); but with the number of teams looking to blow up their crease (TOR, MINN, PITT, NASH(?)), I wonder if you could get a decent tandem goalie on the cheap as teams look to go in different directions.
On wing and defence, I'm not as sold that external help is needed. Rather they need a few guys that can bridge the way until when/if the kids are ready. Think like Yamamoto needing to simmer until new years to break out.
For the McWinger, I still like Benson, and maybe Puljujarvi. (plus both Neal and Kassian can also work well in spot duty)
On defence, I like Jones and Bouchard as puck movers to complement Klefbom, Nurse, Larsson, and Bear.
Even at #3C, I can see McLeod as the man of the future.
Overall I don't mind retaining Ennis and Green on cheap deals to keep the sit warm for Benson and Bouchard. Haas and Khaira will likely continue holding bottom 6 centre roles until McLeod and/or Marody wrestle them away (Though I wouldn't as comfortably bet on that one, as the Benson or Bouchard).
I also expect Holland to go out and grab a couple more vets like Granlund and Jurco. Established pros/vets, but ones you can set down to the AHL (if there is an AHL next year) to cover for injuries later, so you're not thrusting the kids into roles their not ready for. Euro UFAs like Haas, Nygard, and Persson also work well for this, as they can avoid waivers.