The island has literally been rotting in tropical heat for 66 years. I suspect that some of them would invest, but only a trickle would actually move. There has to be a massive gap in IQ between the diaspora and those that remained. What kind of government would be formed? Will we have to prop up a caudillo? Remember we are forty trillion in the hole, and will be expected to rebuild IRAN.
The exception to your observation is quite simple - They never quit coming. All those years, wet foot/dry foot, they risked everything they had and kept on coming. And they didn't come here to get on welfare either. As a people, they work hard.
So yeah. I think the same spirit that drives them to succeed, the same spirit that drove them to come, that same spirit has the capacity for liberty.
And I don't know what government will prevail, though I would suppose, with the US involved, that it will be one that is beneficial to American business interests, which will be some sort of capitalist republic... I would expect a protectorate as a territory of the US, mostly for the ease of raising up a government and a monetary solution, and the long-term stability that would be required to attract businesses back to Cuban shores, but it need not be so.
Either which way, thinking we won't (or ought not to) lend a hand 100 miles off our shores, and at the destruction of the premiere communist foothold in the western hemisphere no less, is almost absurd.
Of course we are going to help. And we dang well ought to.