The post-Soviet "special period in a time of peace" was of course an utter disaster, but the lack of economic competency did not lessen the structural oppression systems that the Castro state operated.
Revolution is going to be hard to bring about at all, really. Class and race divisions continued to function as a way to both perpetuate oppression and sow divisions among anyone who would dissent.
For anything to happen, it'd need outside help. That is just the bottom line. A new Bay of Pigs is out of the works, but something akin to a Contra movement developing is another matter entirely. Of course, with the Cold War over, neither the Bush or Clinton governments would really care that much.
Castro dying however might be the impetus for free market opening or elections. If his death comes from the CIA deciding to actually put their A squad on that old project, the way it is carried out will dictate how things go forward; if its cancer, like with Chavez, reforms likely come but gradually, as the Cuban Commie ruling class will need to get their ducks in a row to avoid what happened in Eastern Europe with the deposition of the nomenklatura. The bottom line is that some tyrants just are good at staying around, or they have such power that the only thing that deposes their system is Father Time. We saw it in Spain with Franco, after all.