Well said,  Eric,  you have a good grasp of Cuba's sad economic and political  history. We remember when drinking "Cuba Libre" meant freeing Cuba from Batista, the Mafia, large plantation owners and possibly the CIA.  Castro's revolution was terrible for the wealthy, generally bad for the middle class, but of benefit to the nation's  poor, who were a large  majority.  The social supports, medical and educational systems are  now superior to most poor nations and would be a great loss to drop them.  
However, their lack of freedom and reliance  on benefits rather than effort will cause problems for change.
We look at the disasters that happened to most Eastern European nations with the fall of Communism, and see many have never recovered.  Our policy of  "shock treatment" to root out their socialism was brutal  in its effects.  
I believe we should be setting up a study group to see how the coming  economic and political changes in Cuba can be guided in more positive directions.