The issue with Milan is that they still lack an actual project that makes sense, and when they do have a somewhat promising project they also have no faith in it and switch it up for something else in a matter of months. Juventus got back from the abyss when they invested in a stadium, they introduced a salary cap, they concentrated on getting young talented players alongside older, more experienced and yet cheap players who are not that technical but are big on teamplay (see Bonucci or Barzagli, the latter cost 300k Euros or so and became the best defender in Italy for years). Milan is simply busy trying to get collectible cards, names like Balotelli, Piatek and whatnot that will sell more tickets, but doesn't solve the defense issues or the mentality. Then of course they get a manager, get him random players, he's struggling for some matches or half a season and bam, you're left home. Not that Giampaolo has a good track record prior to Milan, but if you truly believed in his project and he wasn't plan Z or something they should have gave him a season or two to prove what he can extract from these players, to see by Winter and next Summer where they should intervein to fix the team's issues.
But no, the team is a fucking mess. They have debts up the ass, they buy players without any reason or rhyme, give the old guard pharaonic wages (what they did to keep Donnarumma is comical, they had to hire half of his family in one way or another to assure he stays lmao), then go for inexperienced managers who then don't even get a full season to correct the course of the previous messy cycle. At this rate the team's current leadership will have to step off before any results arrive, and Milan risks going practically a decade in which they occasionally go into UCL or UEL but at no point have a shot for the scudetto - a far cry from what Milan used to be. And as a Juventus supporter it sucks that, year after year, it's been a battle against teams with little winning history like Napoli or Roma, with all due respect. Having a competitive Milan and Inter would render the championships even more impressive. Inter seems to be on the right course, although so far they were going with the enthusiasm of winning nearly every match against easy teams, after which they scored a whopping one point in the 3 most important matches of the season so far (the 2 UCL trips and Juventus in Serie A), so we'll see how they'll manage a potential crisis. But hopefully Milan gets back at the very least to these levels too, because I genuinely feel sorry for the better side of Milan supporters who used to watch UCL finals every other year, and now it's a major party if they somehow get a top 4 finish in the Serie A and don't get eliminated in the group phase of the UCL or UEL.