Maybe it’s just that I’ve been living here my whole life so far and I’m Italian myself. But I don’t like Milan that much. Milan is without doubt the most livable city in Italy, but that doesn’t make it worth living here… Maybe if you are learning Italian, studying fashion or something like that.
Milan’s weather is horrible, people are unpolite, prices are always the highest in Italy.
Also “La Milano da Bere” (Milan by night) isn’t that good as it is believed to be abroad.
Sforzesco Castle and the Duomo are the only two things I love staying in Milan, cities like London, Tokyo or New York are far more stimulant from any point of view.