That's Loew and Tuchel. Most coaches he ever had played Macherano at DM. Frankly most deemed him the best DM in the world. Pep got him and after a few months said, Nah! CB you'd be magic. And He was. Told Lahm, DM for you Sir! And Lahm Smashed the position.
So the idea that it's unlikely he'd play an Intelligent player in a position the player has actually played before, seems strange to me. When he has shown a history of actually not giving 2 fucks about labels.
What if he also gets Isco/Pogba? DeBryune, Isco/Pogba Gundogan. Who do you think is likely to be DM?
This is what Pep does. Sure he might not play Gundogan at DM, but I fully expect him to, and would not be surprised if he does.
Gundogan has not played that role before though, Klopp didn't use that kind of player in his team at all and had Bender/Kehl do most of the defensive work, meanwhile Tuchel has Weigl who plays that part for his team while Gundogan has a license to go forward. Just because he's played deeper in a midfield two doesn't mean he's actually played the role of a defensive player focusing on pinpoint distribution and keeping control of the game's tempo, although he's decent defensively he's always been partnered with a defensive-minded player so that he can also go forward where he's at his best, a mild case of what Pellegrini did with the Yaya and Fernandinho midfield.
Obviously Pep often plays players out of their natural position and makes it work, on top of those you mentioned there's also Messi as a false nine, Fabregas as a false nine and even as a winger once, Javi Martinez, Alaba and Kimmich as centerbacks, the list goes on and on. However that specific role is of such great importance that I can't imagine him bringing in someone who's not naturally going to fill in seamlessly, when you also consider that Gundogan will miss preseason and won't have time to adapt to a role he's never played I just can't see it. Despite having great all around midfielders like Kroos and Schweinsteiger at Bayern Pep brought in an aging Alonso instead, you need to have the right instincts and football intelligence to be able to play like that, it's not something that can simply be taught.
To me sticking Gundogan down there just doesn't make sense, why would you limit a player that can make a run like
this and link up play in the box like
this in a desperate attempt to make him play a way he's never done before when he's got so much more to offer? We might aswell make Fernandinho play the role if we're looking to convert a player away from his natural role, even though he's not ideal he's at least better suited towards it than Gundogan.
Also, let's not talk about getting players like Pogba and Isco when we haven't been linked to them from reliable sources at all this window, we can't assume transfers like those will happen.