This is an interesting thought, but I think it doesn't take into account 2 things. First our young core has no where near developed into the players they will be in their primes. Only Scheifele could be said to have truly entered his prime and he still likely has another level he can reach. Morrissey and Trouba still have room to grow, and especially Morrissey might have a Norris caliber career in front of him. And for our young wingers all have miles to go to reach their primes. A 25 y/o Laine will be a thing of beauty. Helly to will likely find another level with a couple more years under his belt.
The 2nd being, how to make contracts work so as to keep hold of our current vets while the young core develops, and then seamlessly move on from them as needed to meet contract obligations. In my mind there is 2 parts to this. One is to bridge as necessary, and the other is to severely limit NMC's and have the willingness to move a player when they still have enough value that you don't have to pay someone to take them. We will all see how Chevy navigates this over the next few years.