The process of picking players is definitely tough. Good on your for trying to do that and sticking with current players.
The Leafs will be a bottom 10 team in the league again this year. Their defense simply isn't good enough to hang in a playoff race down the stretch. When other teams are required to turn it on, I don't think that the Leafs could do that.
So the priority this off-season will be to shore up the back end. And I think that there will be a lot of moving parts because of the expansion draft.
And I think it's the right time to overpay for a defenseman. And I'm not talking about getting a guy like Manson. I'm thinking along the lines of Chris Tanev or Colton Parayko. The reason that I feel it's a good time to overpay is because I think you've settled on what forwards you want to keep going forward as your core. You've established that with Marner, Matthews & Nylander. The tougher question is what do you do on the back end. I think we've liked what we've seen out of Zaitsev and Rielly. But beyond that, you run into a lot of question marks. Gardiner is dynamic with the puck, but I don't think that Babcock loves his defensive play.
I also think that you need to get good reliable defensive defencemen that can play. Polak, Marincin, Corrado, & Hunwick are all interchangable. If you still want to develop Carrick, then you keep him on as a #5-6 guy and let him play to his strengths. Play him beside a guy like Kyle Quincey, Trevor Daley, or another solid veteran on a short term deal.
My ideal line-up next year would be:
Soshnikov - Bozak - Marner
Nylander - Matthews - Niederreiter
Hyman - Kadri -
Martin - *** - Brown
*Trade Komarov+ Leipsic + picks&prospects for Neiderreiter
Rielly - Tanev
Gardiner - Zaitsev
Daley - Carrick
Andersen
*backup (Bibeau or other cheap 1 yr tender)
I'm not sure the price on Tanev, but I think the Leafs have to realize that they aren't going to get every top prospect into the line-up. So whether you maximize value on Jeremy Bracco because you don't see him in the line-up, or you sell off Andreas Johnnson or Tymashov, I think you need to start to turn the corner with the guys that you selected.