My takeaway from this season is we just need some more experience. That is going to be a tall task when we are likely seeing more veteran players leave this season and injecting more youth. I agree that there needs to be more onus on some of the vets to help the youth find their game but it is a damn hard thing to do.
You look at some of the previous Cup winners and there is always a good mix of youth and veteran players chipping in. I think we are still on that hump. The challenge going forward is will the vets still be good enough when the young guys find their games? On top of that there is still another window when that happens and perhaps a much greater window as you transition from Wheeler, Buff, Little, Perreault, Hendricks, Myers, Kulikov, Chiarot being your leadership veteran core to Scheifele, Ehlers, Laine, Connor, Morrissey, (maybe Trouba), Roslovic, Copp, Lowry and (hopefully Tanev) being your leadership core.
I think at this point we don't expend anymore 1st round picks or go hard at aging free agents. But let that secondary leadership core come into it's own and continue to develop the players we need to fill in the holes for a window of opportunity with them. We gave this current leadership core 2 solid years but we need to realize that the next leadership core coming up is where the real chance at a Cup is. That could mean a season or two on the horizon where things aren't looking amazing and there are challenges and hurdles but in the end we come out far stronger on the other side.