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.

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.

Yeah as someone whose family left this, you guys are crazy

It’s not that easy to emigrate afaik, even ignoring family and obligations like that.

for real happiness it would be the most important thing if not romanticizing.