Well, ask people in Honduras or Nicaragua, which are "free" countries, effectively how much better they have it than Cubans. Hint: they don't, because their countries are "democratic" in theory yet they're overrun by gang violence, misery to a level that makes the worst of Cuba a paradise, and have state actors that claim democracy in theory yet will do what they need to keep their power.

If anything, the history of Cuba's attempted overruns by the US only serve to justify the regime's paranoia.