Wouldn't it be easier to go Uruguay or Venezuela?
I've lived in Venezuela. It is not a poor country. The people are poor, but they have huge oil reserves, diamonds, gold and many other natural resources. They used to be the largest oil exporter to the US until Hugo Chavez started diverting that oil to Cuba for free. Venezuela also charges import duties on all products (with some exception in the state of Nueva Esparta, which is mostly duty free). They also charge an income tax that most people do their best to avoid ever paying.
The real problem with Venezuela is corruption. When I lived there, I did not keep an ID on me at all times, even though it was required by law. I kept my passport in a safety deposit box because it was cheaper to pay the fines for not having proper ID than it was to pay the bribes to get my passport back from the National Guard when they would do one of their regular shakedowns. If you were a mere janitor for the state-run oil company (PDVSA), you were probably set for life. If you didn't have some important friends or family, you probably couldn't get a job for PDVSA.