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Uhm, I think you're overthinking it. There's million other challenges and reasons why you might not like Singapore (or another similar city). If you can and want to go you should go.

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I like Singapore very much! I think it is a very livable city in a fascinating region. They have a straightforward visa process for skilled foreign workers, and a path to permanent residency.

But I'm not interested in taking a ~50% pay cut to move there from NYC when the cost of living is not that much different.

Pay is such a variable thing though. I mean, just being able to move, dealing with everything and ending up liking it long term is such a statistical anomaly that it seems silly to generalize pay (even though there might not necessarily be a correlation between the two). I would at least look into things like working for a US company in Singapore or consulting/freelancing (since the taxes are low?). Often things look quite different on paper than in reality (especially on an individual level).

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