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Nice idea, but the article seems like a paid advertisement for Remote Year and similar programs. Problem with such programs is that you’re paying more than it would cost you to book on your own, and they’re calling the shots as far as location. Probably better to freelance and be somewhat location/time independent than be stuck in what is the equivalent of a package tour.
Yes, the wapo article does sound like an advertisement. Pretty establishment with a nomadic spin to it.
Most nomads do it on their own. Apparently, Medellin Columbia is now a top city for digital nomads. It used it be controlled by drug lords.