I was there last year. The proto-capitalism is happening right now. I was also there in Europe when the East-Block fell. It feels eerily similar.

It's hard to say. Some of the provisions of the pieces of US legislation that establish the US embargo of Cuba only apply while either Fidel or Raul is in power; they are explicitly named in the legislation text, iirc. Of course more legislation could be passed extending those terms to whoever the new leaders end up being, but I suspect (and hope!) it's more likely that the embargo would just end up being loosened somewhat at least by default.