I went to Cuba some years ago, and it was a bittersweet experience. You know, inside the hotel everything is perfect. People is nice, and the tour guide will always show you the good looking sites. Beaches... beautiful, for sure. I found that excessive perfection boring, instead I like to meet the real people and the country itself. But that's a matter of taste I think.
Uutside the hotel walls, some people live with resentment against the Island's unfair system. To avoid unwanted discussions, I suggest you: Do not talk about certain topics (your country, your job) in front of taxicab drivers.
Another curious thing is, instead of begging for money, people asks you for a pen, a notebook, and similar materials.
Cuban Communists are proud of giving free education... But that's worthless if you can't find anybody to hire you. They are swimming on under-employed over-educated people.
Their economy is funny. Do you want to shell your art works? Do your kids make limonade or brownies? Noup, you cannot shell it. People are not allowed to shell anything. Only the goverment can shell goods.