Overpaying and those "extra 5m" here and there are what got us here.
It was the extra money on Paqueta, the extra money on Laxalt, the extra money on Samu, the extra money on Biglia, the extra money that is meant to push through various deals that put us in the terrible place we are in now.
Now, I understand that you can say: "Sam, I get it, but there's a difference between paying extra for Samu (and all those other players) and paying extra for Simakan/Kabak/etc just one time," and maybe, but if that transfer fails, even if they are promising as hell (see: Caldara) the damage is still done.
One of the important data-driven approaches to players and their values is using metrics like their "value-in-use" over a season in comparison to their contract terms in comparison to the "value-in-exchange," basically getting rid of them.
There are various analytics that take this financial approach, which creates a value for a player, and I think our management is driven by this. It's not unique to Milan, lots (but not all) clubs do this now, and of course different data sets will yield different results.
I think for the next few months, the squad is fine according to management. They seem to trust their process--and I guess we will see how right they were. I hope they are.