Maybe I'm wrong but Italiano has some Pioli tendencies
He wants to play his way no matter the circumstance or opponent
Italiano and De Zerbi both have that dogmatic tendency, it's the big hesitancy with either of them.
Italiano has played the same style whether at Spezia or at Fiorentina, against big or small teams. The debate in my mind is: is he held back by the lack of quality at his teams? Like, if he had a top-class striker to finish all the possession and passing, would his style look more like a big time coach at a big time club? Or is he just punching above his weight?
RDZ: is he just using the fact he's at a smaller club with reduced expectations against his opponents? How would he fare at the next level? Does he have a curve ball?
The difference between them and Pioli is that they actually have a dogma to be stubborn over. Pioli has some notion over what he wants to see, but doesn't seem to even understand how it should actually work. He wants his players to dribble and express themselves? Great. He doesn't even know how to shift an opposition to maximize the probability of success for that idea.
Like you, I value pragmatism, and Motta seems to have that, so my slight preference for Italiano over Motta isn't some ironclad line-in-the-sand, I'm just more familiar with him. I'd love to see the experiment of him at a bigger club, I just don't know if I really want that to be done at the expense of Milan with the possibility of it failing.
Pioli's great strength was that pragmatism, losing it hurt the team and which is why we're in this situation.