Democracy is easily manipulated, we live in a so called democracy and look at how quickly it's going to shyt here. The only true democracy is a direct democracy not this representative bullshyt we have that was set up during a time it took weeks for someone to get from Pennsylvanian to South Carolina. Cuba would need to be weened off communism very slowly, or have capitalism introduced in certain sectors but regulated so that foreigners cannot come in and fukk over Cubans. The Cuban govt. has done a lot of wrong, but keeping foreigners at bay from raping the country (specifically US) has been something that has helped that island more than anyone in the news is willing to admit. They would need to have that same mindset with industry & capitalism as they do now keeping the US out, which is - Cubans first. If Cuba attaining democracy is the goal, they should never look to America for help, Canada is who they should use as their example of a socialist democracy.
Also, I know those are your people, but the example of what you don't want Cuba to become is sitting about 760 miles away in Puerto Rico, a country that has $20 billion more in GDP, yet has a murder rate 4x that of Cuba, a lower literacy rate and worse healthcare. The 1% in Puerto Rico suck the US dikk and leave nothing for the rest of the population, with unregulated capitalism the same thing would happen in Cuba but worse, since they wouldn't be under the umbrella of commonwealth.