As a Milan fan I consider myself an expert on mismanagement and mediocrity.
The CR7 return reminded me of our Kaka return in 2013.
A purely nostalgic and idiotic decision which went against the values of the team that had previously managed to finish in top 3.
The 2012 Milan team was a youthful, energetic team which compensated what they lacked in experience and talent with sacrifice and a strong unit.
You were going for high press and then you signed a 37 year old Cristiano Ronaldo?
Another thing which reminds me of our decade long mediocrity is the constant change of systems or "tactical revolutions", new gimmicks.
A classic British manager in Moyes, 90s totaalvoetball with Van Gaal, then ultra pragmatism with Mourinho, "the United way" with Solskjaer, now gegenpressing with Rangnick, next season modern totalvoetball with Ten Hag?
It's as if the club is ruled by the dumber half of online communities, who can't look beyond hype and end product. The players and coaches that the club is signing are the ones that create most fan excitement, initially at least. Corporate people with no football vision.
I don't think you'll get out of this cycle until your upper management give the keys to proper technical directors with a vision that doesn't depend on fan sentiments.
Rangnick was never good as a coach, as Milan fan I'm glad we dodged that bullet. But he might be able to steer you out of this in an executive non-coach role.