Toronto

One of the most well known cities, few will be surprised by what they see and experience. Very high cost of living can make it tough for many nomads. A lot of things to see and do but most of that costs money. Can feel overwhelming and oppressively business oriented (ie, full of very serious yuppies and places catering to them), especially in Manhattan south of Harlem. Ton of single people, which is good on paper but means everyone you date will get distracted by another person, or multiple, unless you are extremely exceptional, before you have a chance to meet again, never ends. Weather sucks hard from July to August and January to March/April. It's an okay city if you're a biker and varies a lot. Some areas are quite protected, others have no bike lanes. In general, it can be dangerous if you want to commute by bike, it's not Amsterdam. Friendliness of the people varies a lot. I think income/wealth, where they grew up, where they live within NYC, their job, etc. can often give you an idea of what to expect. Service at stores is usually pretty unhelpful and unfriendly but, again, it varies, even within the same store. Internet is fast for the most part. Great selection of food, just a bit pricey besides some of the cheaper pizza slices. Transportation system is good, no need for a car. However, the subway lines are notorious for having issues during rush hour and are usually jam packed. Also, the stations look decrepit and are way out of date. It's pretty safe. Street scams are more prevalent in tourist areas, pick-pocketing and random phone snatching isn't really anything most people worry about. Can be very noisy depending on where you live. You may wake up to extremely loud construction every morning.