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I have my own family dependencies that aren't too keen on the idea of living the village life. Otherwise I'd already be there.

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I saw a video of a guy in his 50s living in a small city in Vietnam. He claimed $800/mo was more than enough, and $1000/mo would let him live lavishly. He just did the math and as soon as his predicted months of life left * 1000 < savings he pulled the trigger.

I think about that a lot because I have already hit that number easily, my family would definitely suffer though and not be into it.

There is a reason that South East Asia is popular for digital nomads and for retired expats. Thailand and Vietnam have still very affordable places if you avoid tourist traps. I would recommend first trying some easier destination like chiang mai or danang (if first time in asia), staying for 2 months (vacation/workation) and seeing if you still like it.

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