Do you think they have a better shot than any other country with an explicit firewall (Eritrea, China, NK, Cuba etc…)

I don't think Cuba belongs on that list.

They have limited service because they can't afford anything better, and the USA prevents installing additional undersea cables, but only a small number of sites are blocked by Cuba itself, such as a few Spanish language news sites run by Cuban-Americans.

Many more sites are unavailable in Cuba because their USA owners refuse access to Cuba, but that's not Cuba's fault.