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Singapore wins for liveability, especially as an American. Great food, no crime, and good public transportation. Don't **** off the PAP or cause any problems and you should be fine there. Make sure your place has air-con as well, because living in Singapore without air conditioning can take some time to get used to, trust me.
Hong Kong is probably the most exciting of the cities, very similar to NYC in my opinion. Knowing some Cantonese would be helpful in HK but isn't strictly necessary. The quality of English by all accounts appears to be declining since the British left in 97.
Tokyo is nice, but a little bit different, as is most of Japan.
If I were to live in Asia again I'd go for Singapore & Hong Kong long before I ever considered Tokyo. I can't speak Japanese though, so thats part of my reasoning.
I've never been to any of them, but Hong Kong would be first on my list of places to visit. Singapore to live. I've heard Seoul is nice but for whatever reason, it just doesn't interest me.
It's hard for me to pick. I've been to all of them and I love all these cities except Singapore. Seoul is an amazing city and so is Tokyo but only as places to visit. I'll have to go with Hong Kong and live in a nice highrise.
Tokyo, hands down. 'Course, I live here now. It's got a bad rep due to cost, but if you know where to live and where to go you will wonder how it got that reputation. I've managed to save more money living here than I did after 10 years of living in SF. Trade-off is the language and the people are kind of a steep learning curve for most westerners.
I think Hong Kong would be the best place to be. Language really isn't a problem there and there isn't same level of discrimination against foreigners you'd find in Seoul or Tokyo. The people in Hong Kong, however, have their own style. They are fast, pushy, loud, and generally agressive.
If language was not an issue (able to communicate well in Japanese), and I had a LOT of money, I'd go with Tokyo. Better weather, nicer people (to your face anyway), more culture, and better quality of life than Hong Kong.
Singapore would be my last choice.
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