Actually, while the comments about Milan are true (I'm not a big fan of the city either), they are quite powerful if you think about it.
A relative of mine has many friends living in foreign countries (a few years ago, as soon as the borders opened, many, many people chose to leave and start a new life in Western Europe). While almost all of them are happy and have a better life now, the ones living in Milan have told the truth to the people back home: that the Milanese are not really friendly, that Milan is not your typical safe city, you have to watch your back, that life there is so very busy and tiring at times....ecc., ecc.
The truth it, yes Milan is not perfect, and
@Adam your brother is right, but you know, if the city is so awful, why stay there? There are so many other cities to choose from. I agree there's the finding a new job situation, it's not easy to just leave your life behind and start over (twice, in the case of some people), but you can always choose to move outside the city, there are plenty of Italians who don't live in Milan, they just work there, and they use their cars or the train to commute.
In the end, it's a real shame that the image of Milan is misinterpreted. For this very reason, my brother in law thought Italy was an awful country, full of rude and unfriendly people. And it took him 2 long visits to realize true Italians are exactly the opposite!