I hope Milan, or any team that isn't Juventus, will win the Serie A. As for the winning, we have to see what Juventus will do this season, as they just keep on buying the best prospects in Italian football (Dybala, Schick, Caldara, Rugani and Orsolini just to name a few).
Ricardo Rodriguez, in my opinion, is the best player out of these 4, considering his role. Andrè Silva is a big gamble, whereas Kessiè started off pretty well but didn't shine as much as his teammates when Atalanta earned their access to Europa League.
Just like Manchester City, Milan has to remember that spending more doesn't mean that you automatically become the best team. PSG is a great example of this.