Unfortunately, Milan is obsessed with Inter, and at the start of every season they declare they'll win the Scudetto and that it will be their number one objective. Like every great team, that will be the goal they want to achieve, but unfortunately they don't have the right players for that. It happened once, but in my opinion, it was Inter who lost the Scudetto, and they were incredibly lucky that season with Pioli as coach.
Obsessed with Inter or Juventus is not a problem, because this can be a way to motivate team play well in every match. Unfortunately, obsession will never enough to fix team condition. Coach have role to prepare strategy and bring quality player, but Milan not like that, have obsession to compete with Inter but the player that coach get not match with his need for the team. So, beside coach strategy problem, I believe player transfer process in AC Milan also not maximum.