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.
Strange, all the loops which left wing people jump through, to support murdering dictators... :-(
So, why didn't you compare with working democracies there.. instead of with cleptocracies that had coups and civil wars?
What is the real problem with doing as normal people and condemn all dictators?
Castro had options, he could have gone to Western Europe and asked for help in e.g. the 70s, as part of a democratization program.
(And when Cuba didn't have free money by being a client state, they even had problems feeding the population.)
A trivial counter example -- if you causally dismissed your government as a Cuban in Cuba online, what happens?
(Since Cuba has a really, really strict control of the Internet last I looked, it is of course a bit of an academic question...)
Edit: This comment is really jumping up and down in votes... :-)