Cuba was NOT all that messed up before Castro. It was the wealthiest country in the Caribbean by far, and possibly the wealthiest of all Latin countries anywhere. They had a real middle class.
The education and health systems were excellent--Castro's just taken credit for what was in place long before the "glorious revolution." In 1958 Cuba imported more automobiles than any other Latin country. A quick look at the 1958 Havana phone book will show you thousands of businesses listed, large and small. Today there are NO businesses...no Yellow Pages in fact. Starting a business there is ILLEGAL and will land you in jail. You cannot even grow a sweet potato and sell it to your neighbor without going to jail if caught.
Today, there are MORE prostitutes in Havana than in the Batista days because there are no other places for women to work (and guys too) unless they're lucky enough to have a job at a hotel, which pays $7 per week. Castro collects $50 per week from the foreign hotel company per worker...pockets $43. Batista was NEVER that crazy or cruel.
And as for those gangsters....today every hotel in Havana claims to have been owned by those glamorous gangsters, and you can see photo exchibits on the walls of lobbies and bars featuring the gangsters and movie stars .....they're a big tourist attraction.
Once freed from oppression, the Cuban people will bounce back in a very big hurry. Count on it.
I know the Miami Cubans (they all claim to really be from Spain). It's going to be a huge mess, and it will take them a nanosecond for them to blame the US for not throwing enough money their way.