A lot of the issues you describe seem to come from remotely working in countries throughout SE Asia. What if one were to travel the US as a US citizen? Issues like unreliable internet connection, workplace issues, food poisoning, visas/paperwork, and language barrier would be greatly minimized. Traveling Europe with an EU citizenship would be a similar experience, though you may run into some language barriers. You also have a general idea of what the weather will be like in any of these places.

Overspending on the other hand is definitely something that would be an issue while remotely working anywhere, but if you stay disciplined enough I think you'd be able to manage.