Compared to established democracies in Latin America, especially Central America, like Haiti, Guatemala, Honduras, Venezuela, El Salvador, Nicaragua... Cuba is still a relatively well-off paradise, which no one can deny. Stable, no street gangs, less corruption, no gun crime, no prostitution, relatively good health and education system.
Of course they can do more or less better with some kind of democracy, which I hope. But it is not a guarantee.
With extremely smart, highly disciplined, very hard-working people like North Korean, North Korea can turn into a new South Korea after 40 - 50 years if they open the economy. But with people, who prefer parties, dancing and football than education and work, like most Latinos, whatever the government is, there will be not much difference. At least current government can give a stable job, free education and health care.