It's going to be very strange, since if Communism falls in Cuba, the Communist Constitution will not be in force. The last "capitalist" Cuban Constitution, dating back to the 40s I believe, was in de facto use during the Batista regime, but only when it suited Batista. There will be a legal vacuum in which lawyers and jurists and corporations with no valid licence, precedent or jurisdiction will be operating. It will be a feeding frenzy.

The closest thing we have as a guide will be the fall of the Soviet state,
but in that case most legal institutions retained their legitimacy. In the case of Russia, though, you didn't have a 100K or so exiled individuals storming home with a claim to state assets, so the apparatchiks traded their baggy suits and party cards for Armanis and briefcases and simply took over.

And I believe the second wave to hit the beaches will be organized crime and drug lords.