You're talking to someone who you just met for the first time. You find out that he used to live in New York. You've thought about living there in the past, so you ask him this.
What's it like living in New York?
This is a question you can ask when you just want to hear someone's general thoughts and opinions about a topic. You usually ask people this question to find out about things that you've never experienced before.
What's it like working with Will Smith?
What's it like having your parents live with you?
So what's it like owning your own business?
When the topic is already known in the conversation, you can just ask:
What's it like?
Or for a place:
What's it like there?
You live in a country, a state, province or prefecture, a city, or a neighborhood:
I used to live in Canada.
She lives in Beverly Hills.
Sometimes you can use "live on" for explaining which side of a city you live in:
I live on the South side of Chicago.
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