Countercounterargument:
1. Cuba is deteriorating into capitalism or at least social democracy, slowly, but it is going there. The coups in Bolivia in 2019 and Chile in 1973, and the invasion in Grenada in 1983, are more what I refer to here.
2. The chance of separatists winning a war against the USA, one of the most powerful militaries in the world, unless perhaps backed by another major power (which given your ideology I wouldn't say is likely), is virtually nothing.
3. The CIA would definitely pull a JFK.