I think his two-year extension is a "prove it" deal. A bridge deal, if you will. He has to prove that he's capable of engineering a viable rebuild-on-the-fly, and, two years from now, that rebuild effort has to be in a good place (by Chris Ilitch's standards).
I feel Holland's pretty much taken care of that first part, having made some solid trades and stockpiled a lot of picks and run a stellar 2018 draft and re-signed key RFAs to good deals. The other part, well, we're gonna have to wait and see on that one. Can the younger players take over? Can they drive a dramatic turnaround that sees the Wings return to relevance in the very near future?