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My choices, from "best" to "worst" following your criteria:
1) Buenos Aires
2) Sao Paulo
3) Mexico City
4) Rio de Janeiro
5) Caracas
Buenos Aires is by far my favorite, the middle three are also nice, but Caracas is by far in the last place: it has had a terrible crime problem as of late and is a fairly polluted city. Not to mention that it is probably the least "American-friendly" in the era of Chávez.
Ive been to all the cities in question. My favorite is Sao Paulo closely followed by Buenos Aires. I love the diversity and culture you can get in Sao Paulo. Its definately the most diverse city in South America.
I was stuck between Sao Paulo, Buenos Aires, and Mexico City....but i ended up voting for Mexico City. It might have been the "food" category that won me over. I could probably subsist on Mexican food alone for the rest of my life, with no complaints.
really? as a mexican-american myself, i've never felt that mxc has been underrated by americans at all. in fact, it seems as if americans tend to hype up mxc more so than any other s. american city. or at least, i hear it mentioned more often in my experiences.
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