Ask yourself why it is every one of those nations keeps a very tight rein on whom is allowed to leave the country, whereas the countries of the West have no problem with allowing their people to leave if they want.
Those other nations know that the people would not come home, that they'd rather take up residence in the West, whereas the Western nations know that our own will come home.
What's more, try going to any of the Western nations and hold up a sign on a sidewalk saying that the one in charge is an evil dictator, that the nation itself is a tyranny. What will happen? Nothing...except for maybe a few people looking at you like you're some kind of idiot. THEN try doing that in any of the 'rebel' nations you listed and see what happens. Here's a clue: you won't enjoy it.
Lastly, there's a saying you should remember: "familiarity breeds contempt." It basically means, the more you know of a thing, the less you think that thing is special. You know the West, so you think the West is terrible. You don't know the 'rebel' nations, so you think they must be better. Try living in any of them, and then make up your mind.
To be fair, Cuba might not be so bad - Obama did the right thing by trying to open up towards them, but our Trumpistas and right-wing nut-jobs took us right back to the same insane policy. But other than Cuba, you're going to find out really quickly in any of those nations what it's like to not have First Amendment free-speech rights.