Expat Retirement with soaring?

About Argentina:

Yes, great places to fly:
Bariloche, Chos malal, Mendoza, Jachal if you like the mountains.
Flatlands soaring is good too at south west of Buenos Aires province ( i strongly recommend not living in buenos aires city).
Very cheap to live if your income is in USD.

Bureaucracy is better than it was in 2012. More if you are planing to be here for a while.
Bring your own bird, it is way cheaper, you can sell it to a local when you return and everybody will be happy.
Lots of foreings come with their own glider to fly the Andes.

Like Hank said, you should look for Australia and maybe New Zeland, same language, great soaring places.