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Is Chiangmai in particular especially desirable?

I would hesitate moving to a “3rd world” (I know not all developing countries are the same) long-term as I got the impression once you start caring about schools/healthcare (serious stuff, not getting some routine dental work) they become a lot less attractive.

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I assumed he's single. Asia in particular is lot of fun.

Quite interesting to see (single) Westerners moving to Asia to find happiness, all the while here I'm born in India but had moved to the West to find independence and opportunities. Right now I'm looking towards achieving a balance: get dual passport and live 1/4th of the year in India and the rest in Canada (including other countries).

Works well for me as I prefer, and am happy, to be single.

The western singles looking for that (I assume) are still hoping to make their money in the West (remotely) and enjoy all the western privileges and “eastern” lower cost of living at the same time.

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