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I used to think that Uruguay was at least a little wealthier than Costa Rica, but the latest HDI has them ranked exactly the same. Both are beautiful and (relatively) well-educated and well-governed countries. However, in my case I'd probably go for CR, as it doesn't have the tainted history that Uruguay arguably does: while CR stayed a democracy during the 70's and 80's, Uruguay had one of Latin America's worst "dirty wars" under the civic-military regime of Juan Bordaberry, to the point where at one point it had the most political prisoners per capita in the world!
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