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I live in a quiet town in Phuket for 10 years.
Unless you're a whore monger, Pattaya is a total shithole.
Bangkok is ok, but dirty.
Samui is overcrowded.
Chiang Mai is cool, has a lot of Americans and fairly good transport.
If you want to maintain your quality of living it will probably cost more in Thailand overall.
Money is everything here, if you don't have much you're considered essentially worthless.
Yes you can live cheap, some foreign expats make by on $500/mo, but on that budget you will be miserable.
To live comfortable and do whatever you want as a single person you need at least $6,000usd in monthly income.
If you add in a proper international school etc, you're looking at $9,000usd a month.
Then you need to decide on a visa to live here. several options, none of them cheap.
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