How can I re summarise these in few points
a- Financially AC Milan are much worse off then we are. The days when they could pick and choose the finest players in the world to play for their team are long over. They can't afford our fees, they can't afford our salaries etc. Its like leaving United to join Spurs (and yes Im flattering AC Milan here cause financially wise Milan are nowhere near to Spurs)
b- At top managerial level they are a mess. Silvio Berlusconi shifts between politics, courts and the club and is pretty intrusive in his own way (ie he even lectures managers on how they should play football in front of the press). His daughter Barbara inherited her father's intrusiveness and love for the opposite sex but not his charisma and Galliani was never a great director in the first place. Now a new investor had came in the fold (ie Mr Bee) who will surely want a say. Imagine having Gill, Woodward, Edwards and another person fighting with one another on whom United have to buy, what strategy it should take etc.
c- Darmian will soon learn a lesson Di Canio, Ravanelli and Vialli learnt before him ie that there's a better life-work balance for footballers in Britain than in Italy. In Italy football is everything and when results start getting bad the players lives can easily turn sour (ritiri etc). In Britain players are more protected especially at a club like ours
d- Ironically Darmian will add more years to his career in Britain (as a fullback) than in Italy were they usually play with the wingback role. As Gaz said going up and down the flank as a wingback is very tough and requires plenty of stamina and leg work
e- Darmian was brought up looking up at the likes of one club legends such as Baresi and Maldini who were cheered and loved by the fans. He can achieve that at United if he can stick to the place. After all we love our fullbacks just as AC Milan fans do.
I am not saying that we're completely out of the woods. If Real or Barca come knocking at the door than he will certainly think about it just like all the rest of our players. Also if we leave him with just 1 year contract left than expect the Italian clubs (expecially Juve and Milan who are experts in the matter) to grew bold and try to sign him up. However I am optimistic about the guy remaining here. Real-Barca doesn't like spending crazy money on defenders and the Italian clubs are nowhere near us in terms of finances