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Maybe. But they are not free to leave, which has always been a basic human right everywhere but in the most totalitarian nations. Is it your understanding that Cuba has a higher standard of living, or a better educational system, than Guam or Puerto Rico?
Standard of living is dependent on the demographic tested. My contention is that we'd probably benefit more from Cuba where the majority of the population is educated than a place like Guam where most are dependent on US charity. They have a native population that is far more educated than Puerto Rico's. Why not take advantage of that?