Nick Miroff has a great take on the current state of the revolution in Cuba. The basic takeaway for me is that whether you like it or not capitalism has already won. Incidentally, this is true all over despite all the rhetoric about revolution, Che Guevara, imperialists, socialism or death, etc.
Cuba today is a place where many young people idolize the United States and display little patience for the state-run economic model that has left much of their country in ruins. There is no stigma anymore toward entrepreneurship or private business. Real estate agents in Havana’s newly liberalized housing market signal high quality with the phrase “construción capitalista,” meaning a property that was built in the pre-Revolutionary period, when people cared about aesthetics and workmanship.
For U.S. policy toward Cuba to succeed, we need to treat Cuba as it is, not as it talks. After all, the Chinese still talk about Communism in a way that everyone understands is false. What will replace the old-style revolution is anyone's guess, but the command economy stopped working a long time ago, even if some in the U.S. won't accept that. The hopeful result is social democracy, where the real gains of the revolution--health and education in particular--are protected and maintained.
The best strategy for the United States is to engage without interfering. Cuba is moving in this direction on its own, and Venezuela's slow collapse is contributing.