Trains are on time to the minute, and delays of more than a minute are rare and frowned upon by the transportation agency, the news, and the public. Trains will take you literally anywhere and everywhere in Tokyo and all of Japan.
Tokyo, like the rest of Japan, lies on the Ring of Fire and is prone to fairly regular earthquakes. Most are small, but once in a while, residents do get shaken up by a slightly larger one. Most of the buildings are built to withstand earthquakes up to a magnitude 8.
Toronto is one of the most multicultural cities in the world, with over 140 languages spoken.
There are festivals and celebrations frequently with roots from all parts of the world. You can read more about the diversity statistics here.
Toronto has weather that you probably expect from Canada. Summers are very hot and humid, while winters are cold and gets a fair amount of snow (100+ cm/winter).
One of the most important centers during the Renaissance and one-time capital of the Roman Empire before that, Milan has always been an important cultural hub. Because of this it's a city rich in architecture, museums and history.
Nowadays it's famous for being an important center of fashion and design, the Milan design week is the largest of its kind in the world. Also famous for the prestigious "La Scala" opera house and home to two of the biggest European Football Clubs.
So wherever your interests may lie (history, architecture, design, fashion, music, sports), you can most likely find it in Milan.
Once you've mastered the subway system, getting to anywhere in NY is a snap. There are over a dozen routes operating 24/7 to get New Yorkers to all five boroughs.
People speaking every single language, eating every kind of food, doing every kind of job, wearing every kind of clothing, playing every kind of instrument, the list goes on. New York is home to everything except deep dish pizza.
While posh areas like the Upper East Side are very clean, the majority of Manhattan is rather cluttered. The subway system in particular is known to be the home to thousands of cockroaches and rats.
Locals have to learn to wade through the waves of tourists on every block. Particularly congested areas include Times Square and the immediate radius of the Empire State Building.
Property is cheap and the cost of living is minimal compared to other cities. Restaurants are abundant, there are museums and plenty of sporting events and the city is small enough to easily get around. Overall it is a pleasant city that is easy to live in.