Different governments have brought different standards of living to Cuba.
The American occupation was a disastrous time for many Cubans. The War of Independence had left the country in ruins and most people were without jobs.
After the occupation, various Cuban governments took over. For the years until the Revolution, most of the governments were highly corrupt. Winning the presidency was often seen as an effective method of getting very rich.
As a result, little was spent on education, health care, building the economy, and helping the poor. Many people worked in foreign factories, on what little land they had, or tried to make their living in the cities. Few were able to enjoy a prosperous life.
Given the similarities between the policies of these pre-Revolutionary governments, the standard of living in Cuba remained poor.
Things eventually did begin to change though. When the American Mafia and US companies came to Cuba, tourism flourished.
This added greatly to the Cuban economy. A middle class started to develop in Cuba and it eventually accounted for about 30% of the population. However, the main benefactors of investment and tourism were those in the United States.
There were still many people in the country and cities that had a very low standard of living. Tens of thousands in the cities were beggars or prostitutes. Rural areas were completely cut off from development, education, or health care
Fully five million people did not have access to electricity, running water, or sewage facilities. Many peasants were without needed land or any way of making money, and many of their children couldn't attend school.
After the Revolution, much of this changed. The new government built 10,000 classrooms in just two years. Rents were cut in half, and a maximum amount of land people could own was established. Tremendous gains in health care were made, every Cuban now has access to a doctor and the medical services they need.
If the future brings political change, it will surely bring change to the average Cuban as well.
A return of those who prospered during Batista's years would surely mean the end of social programs from which all have benefited. However, it would also mean a huge boost for the Cuban economy through tourism and US investment.
Much of this economic gain would flow into the hands of foreign capitalists and a wealthy Cuban elite. Most certain to be hurt would be those living in the countryside. Those in cities would have a greater chance of profiting from tourism, but it is hard to tell if they would gain as much as they would lose.