If you're thinking of Chile, you should talk with @hilarski who lives there with his wife. I have never been but many of my friends say it's really nice. I have been building online businesses for a while and keep working towards portable income sources too. Meanwhile, I will sell timeshare in Mexico, a great way to make a living there for an expat. There's lots of expats doing that there.
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Hilarsky is in Panama,
I've spent a few months in Chile and have a few friends there. It's probably the softest landing for us outside the US.
That's right, he is. What was I thinking? Someone I follow is from Chile. Can't remember who right now. You were making a move too right, or already did?
We actually were about to buy our tickets when EscapeArtist had assets seized by creditors. It kinda put a damper on our plans. :/
There are a couple of folks here that are in Chile. EscapeAmericaNow, PiedPiper, Gringaliciouis and RigaroniB (I think) come to mind.
@gringaliciouis, that's who i was thinking of. Love her food posts.