LONG…
Summary: I would consider Uruguay now, but would not live there if I were young.
START:
This kind of depends, but probably Uruguay if I could get a place close to the water north of Punta del Este, because (unfortunately) I am getting older.
That said, if I could do over where to live from 2007 to 2014, there is no way that I would pick Uruguay. It is just too slow and boring.
I never visited Montevideo for a night out other than one night in the middle of the winter in 2008 or 2009 when I was in a “visa run”. (Bouncing over to Uruguay so that when I returned to Argentina I got a tourist visa stamp for 90 more days.)
That night I met some young people (college age) and went out to where the young people (16-22) bars are and I was way too old for that scene.
Other than that, I don’t know.
Montevideo does have a small “Beach front area” similar to Santa Monica down to Marina del Rey in LA with a bike path, volleyball nets, and new apartments/condos, so maybe you can find a nice life there, but even though I can’t afford it, I prefer the Punta del Este and north up to Jose Ignacio and beyond.
The chaos of Buenos Aires can be fun/exhilarating, especially if you don’t have kids. If you don’t have to worry about how the next election is going to affect tour future and you can just focus on eating well, trying to hook up, doing whatever chemical stuff you like (coke, ecstasy, powdered Molly, acid, and/or weed were definitely at almost every party of expats that I went to from 2008-> but I didn’t realize if for a year or three because I never dabbled in most of those things before, so I didn’t realize it). coke was US$15/gram… which I believe is not very expensive.
There are gated polo communities in Argentina and a ridiculously gated community “NorDelta” that offers boat slips at many houses in the greater Buenos Aires area.
Argentina’s beach zone is south of BA about 3-5+ hours and is cold most of the year
Córdoba is the 2nd biggest city and has nice commuter towns as well as a Lake District, which is cool. (Lots of pre & post WW2 German culture in that region.)
Uruguay is developing vino tourism, their beach development is stretching all the way up to the Brazilian border, is has less crime and legal weed (not just decriminalized).
Basically, give me a fun, smart, attractive woman who likes to fuck and try new foods and good weather and I could be happy wherever.