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Re: Why Not Annex Cuba?
Setting aside the military arguments, there are a couple of socio-political points that would make this a difficult proposition. First is that, for fifty years, Cuba has been filtering out those who would want to live in an open society such as ours, either by killing them or failing to prevent them from emigrating/escaping. The majority of those that are left, we can assume, are people who have found some accommodation with living in an authoritarian society. It is doubtful that they would adapt well to a citizen's role very quickly.
That would require a long period of time with Cuba as a territory. How long? Well, Hawaii was annexed in 1898 and made a state in 1959. Puerto Rico was acquired about the same time, and is still a territory. A century for Cuba may not be long enough.
Finally is the gordian knot of competing property rights. What do you do to resolve the issue of property seizure by the communists, assuming you do anything? And what would be the political blow-back if you did nothing? After our recent "nation building" adventures, I don't think it would work out well for anyone.