In the 2000s I did an Argentina version of what you're doing, and getting accommodation was such a PITA -- there were some services in the middle to help match-make but they took such a massive cut. The "rent from some larger org, then arrange something with the owner on the side" is still the best way, apparently.
I don't mind middlemen, but I do like them to provide some value and not just rent-seek.
To me, just talking with people (locals or other expats) is the best. Markets are more chaotic in Latam, a lot of options are not listed online, that means there are good deals to be found.
George Gammon has made this a business with real estate in Medellin. He finds and buys bargain properties via informal connections, improves them and sells them to expats online.
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There's such a massive opportunity in LatAm for people with super fluent Spanish and a deep understanding of the local circumstances (which are often rife with corruption, requiring bribery to get required legal permits, services, etc. to happen in a timely fashion, or at all) to serve as an interface with gringos.
This is what I meant by the middlemen I'm happy to pay for -- by all means, help me get my internet up and running in less than six months! I'm no longer in a position to occupy this niche, sadly.
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100%.
Here there's actually not so much corruption, but what you said about understanding the local situation is spot on. Not everyone can do this. You have to be patient and smile a lot, invest in connections.
Anyone interested in these opportunities, happy to share my ideas.
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