I'll keep it brief, but knowing Cubans who left Cuba, and asking them about it, it's extremely repressive towards its citizens. One of my coworkers, who is in his late 30's, as well as my boss, who is in his late 40's, tell me the stories of what a police state it truly was, and remains, and how speaking out against the government, or even being caught with U.S. Dollars would land you in jail for inordinate amounts of time.
People fled the country, leaving all but a suitcase behind. They still do. That says something. They're leaving 99% of what they have to escape the regime there. Some bribe officials, if they have any wealth, as I've been told, and some try to make it over to Florida on boats or rafts. People don't leave the U.K. for N.Z. and have to leave their wealth behind.
Havana is supposedly a fantastic place to vacation, which is in stark contrast to the living conditions of the people who work there.
Without getting into politics, I don't know why the U.S. still enforces an embargo on Cuba while having free trade with China. IMO, the Cuban-exile voice in South Florida is disproportionally strong when a small number can dictate an entire nation's stance towards a country.