This subject came up in a PM today... it's an interesting discussion... here's my dos centavos...
Even though I've spent a considerable amount of time in Cuba I could never live there for an extended period and I could never consider it as a retirement option.
A few (of many) issues for me: Can't own property... can't buy a vehicle... telecommunication infrastructure horrible... crap Internet... if you're into variety it's difficult and expensive to buy/cook your own food... banking is a joke... news sources all government controlled... satellite dishes illegal... health care is generally very poor outside of tourist centres... the beer selection is horribly boring... Honestly, the list is endless.
The people, the general safety, culture, music, etc. and all the other MANY positive aspects that I adore simply can't overcome the glaring negatives for a long term stay.
That said, it's entirely possible (I've done it several times) to find an area you like, rent a long-term casa and "kind of" live like a (rich) local for a period of time... but it will be much more expensive for a lot lower standard of living than in countless places throughout Mexico and Central/South America.
What do you think?
TerryEdited: 2:16 pm, September 11, 2012