Milan Management
According to Corrierre Della Sera, Fassone will meet Maldini next week about a role.
Corriere Dello Sport has a headline that Maldini's returning and his role will be as a General Manager
Fassone has apparently offered Maldini a role as technical director:

However, before there's too much excitement Maldini is going to think it over the next few days, but Milannews is pessimistic saying that he's unlikely to accept as he wants a role of greater responsibility.

I don't know what role he's been offered (technical director in itself is pretty meaningless), but he's always been adamant he would only accept if he's offered something where he can make a difference.
Technical director is meaningless? What else is there available besides CEO and president (expecting Chinese representative and/or Fassone to vacate their spot for Maldini?)? I will be the lone Milan fan to say former legends are being selfish if it turns out as it looks like in the past month (Albertini story, this story, etc)
Why do you think a technical director is meaningless Dev? What do you think will be a step up from that? I can only think of 3 positions higher....owner/president, ceo, and director of football/sport.

It all depends on the description of what he'll be doing because there really isn't a great definition of what "technical director" is to be honest. You can basically call any role technical in some terms, but i doubt it's something irrelevant.

But in all honesty, as much as I love Paolo....what the hell does he want? He wants to just be the top dog immediately? It's not like he is going to be a dishwasher ffs. You gotta start somewhere and this is still the role of a top executive. I will be seriously very disappointed in him if he turns this down.

Edit: like Reza said....our legends are acting like little spoiled children now. In a time when it will be essential for them to carry the "Milan genes" forward into the new management and preserve the club culture....they are acting like fat kids in a candy shop, posting "I'm not an Interista" posts on twitter. How spoiled and stupid...
Does Maldini want Fassone's job? What is he thinking? And I don't even want to get started on the stupidity of Albertini's comments...
Sorry I didn't explain what I meant, but basically all I was saying is the job title in itself means little to nothing to me right now, the key is in understanding what the actual role is (which we know nothing of) and what duties and influence he would have.

If he's been offered a role where he's working collaboratively with the new management team and the decision making process is shared, then by all means I think he should take it up. If the role is one of vanity where he has no actual influence and he's there for the public eye, then he's IMO correct to reject it.

Based on the latest article on MN he wants to effectively replace Galliani and be the decision maker. If this is the case, then I don't agree with him coming because I don't want autocratic rule, I want a modern management structure with shared decision making.

My guess is that the truth will be somewhere in the middle on all this, that he's been offered a role of some value, but he still questions aspects on the role and ultimately what contribution he can make.
While Galliani type power is poor for reasons we all know so is also having 5 vice GMs or presidents (or something like that). Frankly the way it sounds may be below Fassone there should be no one but scouts, real scouts of course.
I've always felt this way and I still do, while I would love to see the old legends return and represent this club again, I just don't find it to be the most important thing for us moving forward.

While I totally respect the intelligence and smarts of Albertini, Maldini and the rest, I do wonder how come none of them is employed by another team in some management capacity. Is it because they are so loyal to Milan that they just cannot bare the thought of working for another team? Or is it because other teams don't think that highly of them that they do not want to give them an important role? Or maybe they are just not motivated enough to work their way up? From my perspective, a guy who has almost no managerial experience cannot and should not be handed an important role within the decision making branch, no matter how smart he is. Management is more than just intelligence and smarts, it requires seasoning to make everything function smoothly. Just because you wore a pair of cleats for 20 years does not make you a super manager all of a sudden.

At this point, we are probably better off just getting professionals to do the jobs we have opening. Old legends can come back and be a part of the family if they want to, but I really don't see them being all that motivated at this point. And the cocky, full of himself attitude is something this team does not need anywhere. This isn't the Berlusconi Milan of the 90s, where everyone can stick their nose in the air and act like they are the biggest thing since sliced bread. This Milan needs to be a workman like environment where everyone is willing to work from the ground up to build an empire.
Look at it this way. This new era might be a fail when we look back in 5,10,20 years because of either Fassone, the Chinese or both. But if Fassone is indeed given the major role others should work with that, actually the legends must be more willing than nobodies to be part of this new era, in almost any capacity. Another example: It's like seeing Maldini refusing to become Milan coach because his say in transfers will be limited ... that would be very wrong of Maldini.
You're right Reza, having no hierarchy is just as damaging as one man controls all, but honestly right now we have no idea what sort of structure the new Milan management will have and I'm neither going to condemn nor promote Maldini's actions here, I'm simply not at all sure what the negotiations are, nor what's right or wrong.

Going by the latest rumours:

- Maldini and Fassone have spoken a number of times already: This can actually be seen as a positive, as if negotiations seemed unrealistic or unlikely, I doubt we'd hear anything. The fact that having already had discussions and have allowed this to go public means there's probably some optimism on an eventual agreement.

- Work with Fassone and Mirabelli on sporting decisions, including transfers in and out: This one is key imo and possibly the most difficult to manage. Maldini working with Fassone and Mirabelli on decision making is ideal imo, as I said before, with them reporting to the owners (Han Li or Yonghong or whoever) with their decisions. However, the biggest sticking point here, if rumours are true, is that Maldini wants freedom to make his own decisions and to have direct contact with the Chinese. The first, I think he'd need to concede on, as it should be a collaborative effort and a joint decision. However, I wouldn't begrudge him for showing hesitancy at a great level. Fassone and Mirabelli have a history of working together, Maldini would come in from the outside. On top of that, it's obvious that part of the decision to bring him in is his image in the public eye. If Maldini's not careful, he could be brought in for a face and ultimately be left out of decision making, especially if he only has the option of reporting to Fassone. There's a lot of politics involved in business management, so it's understandable there are doubts if you're making such a massive decision.

- Representative of Milan at UEFA and the ECA: I'm very "meh" on this one, it's using his image for the club (which is common), but not likely utilising his skills or talents.

Responsible for the management of the new Italian and foreign arrivals: This one makes complete sense, Maldini managing the players seems natural and I think should be one of his responsibilities.

- Manage the official executive team, with the possibility that he chooses all the other legends to work for the new Milan: Not sure what "executive team" means in this context so no opinion personally. "Possibly" giving Maldini choice on which legends can come and work in Milan feels kind of empty and pointless, because firstly it's not guaranteed and secondly there's no idea what role they'd have, it could be simply a nothing gesture to allow Maldini to have his friends back in Milan (something I disagree with as I want qualified people).

There's also disagreement on his pay, though no opinion personally as we have no clue what figures have been discussed.

I think as I said before, there's probably a lot of sensationalism going on in the press with the reality being somewhere in the middle.