Getting tired of this discussion.
It's simple. The core questions are few and only those matter right now.
What is needed for success? Competence and continuity above all. Money and luck albeit being important factors are outside the equation.
Since continuity is one of two fundamental pillars we should start by looking at what we got.
The questions are then:
1) Can Boban, Maldini and Massara provide further continuity?
2) Does Boban, Maldini and Massara have enough competence?
The answer to question 1 is a no-brainer.
You can't even imagine a duo (or a solist) who could be in a managerial position with more ties to the club.
Given their profound ties to Milan they would never sacrifice sporting success for short-term economical benefits/professional directives more than what is absolutely necessary. This is a very important point.
The answer to question 2 is trickier because competence is determined by success and success can only be determined afterwards.
The things we could look at which could give us some ideas are:
A) Their résumé
B) The choices they've made so far. Not only in terms of signings but also their general ways of reasoning and handling different/changing circumstances.
C) Exceptional personal traits
Regarding point A there's a concern because both Boban and even more so Maldini doesn't have prior first hand experience of their current positions. It is important however to not assume this equals less insight or competence. Boban wasn't just an outspoken analyst, he's also been a very succesful director during an important institutional career, echoed by the praise of many professionals including the FIFA president who openly expressed his sadness over Boban's departure as well. For what it's worth Costacurta also said that he's one of the most educated people he's known in the world of football and that he knows the environment. A résumé and reputation can only tell us so much however. People can be succesful in one context and not in another.
Boban's institutional experiences (coupled with Massara's) is valuable nevertheless and it surely provides a bridge for Maldini to the practices of the institutional world. Once you do know the practices and ways of the field I don't think experience is as important as many people seems to believe though. It's not rocket science after all. What is more important is the character and judgement of the people in charge. You can always learn the common practices and ways (if they aren't already clear) but how many sporting directors do you know has gone from being shit to great because of the amount of years they've spent on the managerial field?
Regarding B) I think it's important to look at their general approach because of the small amount of data. As always not every signing/appointment will be a success and with the limited amount of data it's difficult to reach any certain conclusions. Just as we shouldn't legitimize them because of Rebic's and Theo's success we shouldn't dismiss them because of GP and Duarte. What we do know is that they have operated well with limited resources and worked hard on getting rid of the right players, they seem to have a clear view of what the team needs. We also know that they aren't stubborn and will act when it's needed, as they did with GP.
C) I cba to write about this tbh but I'll mention that Boban has/is probably useful when dealing with UEFA and their constraints.
When it comes to Maldini I'm sure many dismisses other's appreciation of his presence as an expression of nostalgia. Nostalgia certainly doesn't help the team evolve but his presence surely means more than that. Besides some players already mentioning his importance during their transfers Maldini, being the embodiment of the club that he is, also acts like a glue/bridge between the players and the soul and meaning of the club.
Tl;dr: Stick with Bobin
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Picking this new page. Sue me
