My feeling is – why wait? No I am not suggesting anything military-wise.
The US should simply end the embargo of Cuba now and let the economic and social connections start to grow between the US and Cuba naturally and privately. The US should respect all existing ownership/property as they exists now…the claims of those who fled should not be supported – but any claims post-embargo should be.
The US can open an embassy or consulate – but this should not be a US government effort for the most part.
It should be the effort of US companies, social groups, churches, and individuals all with there own agendas, goals and incentives.
The US should not fear Cuba anymore. It is not destabilising the Caribbean or South America or Africa. It is time to start connecting Cuba to the US.