Now what I'd love to do is go live somewhere cheap overseas if I could get interesting work outsourced (esp. development of significant JS software), but that sounds like a pipe dream.
Its safe, more organized than most of the US cities ive been to, and it has a thriving and friendly tech community if you dont want to completely remove yourself from it.
If you seriously want to pursue this, let me know, I lived there for some time and have very good contacts w/ the startup/tech community and in education.
I suggest you read this article: http://www.techcrunch.com/2009/10/10/chile-wants-your-poor-y...
(I'm not Chilean, no agenda here)
To get enough jobs to support yourself, you end up undercharging. And the business can't scale because most people you'd consider subcontracting to either charge astronomical rates or are god-awful: There's a surprising dearth of people who know their stuff.
As for teaching English, the best thing is to just go to a country you are interested in and look for work once you are there. I taught English in China last year (along with doing freelance work) and this is how I did it.
You could find work before going but this is actually riskier. They will most likely lock you into a year-long contract and there is a lot of bad schools that recruit this way because the candidates do not know any better. It's much better to move to a place and spend a month looking. That way you can talk with other teachers, see how the school looks and make sure it is not in the middle of nowhere.
In many developing countries you can live well on $500 a month so freelancing is always an option for you again if teaching isn't for you.