I don't disagree about your analysis of the politics but I still think the math just doesn't pencil out. On the other side of the issue from all those Cubans who don't want normalized relations is business interests that do.

Levis wants to sell them jeans. Apple wants to sell them phones. GM wants to sell them truck. Raytheon wants to sell them radar systems. There's just so much money to be made when a formerly isolated market become unlocked that I think you could win back Florida and more with all the donations from the big corporations that would stand to benefit from normalized relations with Cuba.

I think the only reason nothing happens is because there's no one sector that really stands to benefit and can make a concentrated lobbying effort whereas the people that don't want it are a unified ethnic group which for the purposes of high level political analysis can roughly be seen as a voting block.

Ditto all this for Iran, but move all the decimals to the right once or twice.