In Brazil, a few years ago, there was a case of a federal university that purchased Dell workstations for their labs.
Dell told them to stop all relations with Cuba, including academic research as otherwise they wouldn't be able to fulfill the order because of the embargo.
Even though the Brazilian arm of Dell is a Brazilian company, registered in the country and has to follow Brazilian laws, Dell US would be sanctioned if they allowed this transaction to happen.
Last I heard, Brazilian Ministries and the Federal justice system were sueing Dell Brazil. I don't know what was the outcome and could never find information on it.
Sure, they could try to source their lab computers elsewhere, but do you know of any computers that are 100% US-free?
which TL;DR states that it is easiest to trade the most with your largest neighbours. For Cuba, that means Florida (and after that, Mexico and Central American countries). Yes Cuba _can_ trade with more distant partners, but it is less preferable.
https://en.wikipedia.org/wiki/Gravity_model_of_trade
https://www.economicsonline.co.uk/Global_economics/Gravity_t...
E.g. China cannot import some items from EU, although they are not under EU sanctions, but because USA effectively controls EU and prohibits trade of some goods with China.
Same with Russia. E.g. every time Russia tries to sell weapons to some third country, USA attempts to create a pressure to cancel the deal.
I'm sure Cuba suffers from similar restrictions.
Anyway, no matter what you do, an island with almost no mineral resources, no source of energy, will always suffer. It doesn't matter whether the government is capitalist or socialist, what currency you use, whether there's embargo or not.
People living in Cuba will be always poor. It's impossible to change that because it would contradict fundamental laws of the universe: you need resources to grow, you need energy.
It's just that now all of them have more or less the same income. If they'd return to capitalist system, very few will become extremely rich (drug suppliers, brothel owners) and the rest will become extremely poor. Just the way it was before revolution.