That is truly hilarious. There are numerous countries, especially in Latin America, that can tell you a story or two about what happens when free and open elections fail to lead to the USA's chosen candidate winning. It's not sanctions being lifted, that's for sure.
Also,the USA cares absolutely nothing about democracy in their partners. Never has, still doesn't. One of the USA's biggest curent allies is Saudi Arabia, one of the least democratic nations on Earth.
I said exactly what you said: the regime is fucked and the economy will suck and things will be oppressive even without the sanctions.
But they use the sanctions to legitimize themselves. I've heard it directly from Cuban apologists... And in the meantime Cubans suffer.
Regime change via sanctions isn't going to work. 50 years of evidence can show you that. So what are they for?
Removing the sanctions removes one excuse among many that the dictatorship uses.
This isn't China. It's a tin-pot dictatorship on a tiny island right off the US, dependent on tourism.
As for your argument around legitimacy, it does not matter. They will find an excuse to legitimize the government no matter what. See what venezuela did when we still had relations with their government.
All this talk of legitimacy actually just does not matter. Cuban people know their government sucks and if they havent realized it already they are too deep in the propaganda to ever be convinced
edit: Also out of curiosity, if this was a fascist dictatorship on the border would you advocate free trade?
Your mindset is that Cuban suffering is because of US sanctions. How about having the mindset of the leaders looting the country causing Cuban suffering?
As someone that is self-admittedly a leftist, why do you put 0 agency or blame on the leaders of Cuba? All they need to do to have trade with the US is to have free and open elections.