If you look at the player Sterling is now to the player we bought from Liverpool, it's chalk and cheese. He's gone from a very raw, immature, tactically inept winger who didn't know when to pass, dribble, shoot or run and grown into a very assured, technically confident and tactically astute winger who knows where and when to run, when to pass, when to attack the fullback and when to hold his position to create space.
If and that's a big IF Pep can work his magic on Bailey in the same way he has done with Sterling, Sane, Coman etc. then why not. I personally think there's better options right now but what I want from a winger and what Pep wants might be two completely different things and who am I to argue with the man.