When it comes to Cuba, and Israel's enemies, for that matter, our tendency in the U.S. to demonize ends up causing us a lot of problems. Cuba's government is a family-run dictatorship on a poor island. It is a complicated affair because the people on the island themselves have a lot of mixed feelings about their situation, kind of like people in a dysfunctional family where there are parents who may be way too harsh but insist they are doing it for the kids' own good. But Cuba remains a culturally vibrant place with a very high literacy rate, for instance. We are not doing anybody any good by insisting that, in our own view, it is the monster under the bed and it needs to be feared and isolated.
Here is a link to an article on post-Fidel Cuba. The author is on the faculty at the University of Nottingham in Britain which has a Cuba studies program in partnershiip with the University of Havana.