The answer is probably not, because I doubt I'm going to have any response that deflates a lifetime of American culture and propaganda, but I'd like to know if y'all have made any success.
I ask because earlier today a person I know came to me, asking if I knew about what's going on in Cuba. I answered there's a kind of small anti-government protest alongside much larger pro-government demonstrations. This was immediately flipped as proof of Cuba's tyranny, since a large pro-government demonstration means everyone's afraid of being jailed or executed. I tried mentioning Cuba has a pretty popular government, the vote on the constitution seems proof of that, but that also just gets flipped as proof of tyranny.
I don't know, it was frustrating and I otherwise respect this person. Have y'all been having trouble?
Say the best thing the US can do is end the Blockade. While you can say you don't think there is a dictatorship, you can say that if there is a dictatorship, ending the blockade will prevent the US from being used as an external threat to justify their power.
To play devil's advocate, ending the blockade could be a disaster for Cuba. The Cuban government could liberalize like the Russian government did in the 90s. Like what if Guantanamo was made into an American Hong Kong or West Berlin? All that foreign capital in Cuba would challenge the power of the communist party and it wouldn't be long until we saw a McDonald's in Havana.
Ending the embargo doesn't mean that Cuba will immediately have free trade with the US, much less free flows of capital. It just means that the US would no longer attempt to prevent Cuba from conducting transactions with other nations.
Cuba could end up allowing foreign capital (like China), but that's a political issue, and one for the Cuban people to decide on. Personally, I trust the Cuban and the Communist Party to protect the revolution, like they've done for decades.
Being able to trade isn't the same as engaging in completely free trade like you just described. NOw, any company that wants acces to the US market refuses to have any form of interaction with the island, or else they get massive fines, or might even lose theor acces to it altogether. Like this Dutch bank and this French bank for example.