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I don't think language is such a barrier, plus your english isn't that bad either. However I do think it is about opportunity. It really depends on how much you can take and to give for adopting a new environment. However though, I think overall the rages in North America are quite high. Keep in mind though things do cost more here in North America. If you were to go to school you could still work at a restaurant to support your living until you done school, I don't think getting a job is that hard (if you're not asking for a lot). This is what most immigrants / new comers face when they first landed in US/Canada. They might not always get the job / salary they used to have back in their home country. These are things you should consider and be prepared if you were to move to US.

If you are not too sure about what to do yet, why not wait for another year or so? I honestly don't think sending your son to the states at the age of 2 or 5 makes such a difference. Kids sure get use to new place a lot better than adults.

As for living, I don't think $1500 can get you a nice 2 bedrooms in NYC. I don't live in BYC so I'm not 100% sure. However, say for here in Toronto, living in the core of downtown in a 2 bedrooms condo costs over CAD$1600 for a decent one. Therefore I'm assuming it will be more expensive to live in NYC (?!). I'm sure if you are to live in MYC you would want yourself and your family to live in a safe environment (no offense but nyc does feel very unsecured for me..), so I'm not too sure if the $1500 will do the job...

Overall just keep in mind that once you gave up your job / statues in Hong Kong, You may never get them back even if you do decide to go back. The work environment is very competitive in HK. It might be an illusion for me (personally) but I do think younger people in Hong Kong get more opportunities. Anyway good luck to you and give yourself and your family a bit more time to think before having to give up anything!