I know I left the question very broad. At the moment, I'm researching my options of where to go. I'm not tied to a specific location like Europe or Asia or more specific: working in Madrid vs. working in Tokyo vs. working in Santiago vs. working in Vancouver. Each of these locales have their pluses and minuses.

I can consult numerous guides on living abroad in all kinds of locales as well as read various blogs on this topic.

I am more curious about how the HN community members made it work for them, independent of their locale.

As for "every country would be a different answer", why not have every country listed here?