I recall visiting Cuba during the second term of Obama (shortly after his visit) and seeing the various reforms that were taking place and feeling very optimistic about the island's future. We saw a lot of highly political art on display, ate at some of the first private restaurants, watched a helicopter explode overt the ocean as they were filming a Fast and Furious film, and went to a nightclub/art show event that rivaled anything I've been to in NYC.
In a sane world, we would be Cuba's largest trading partner and largest source of tourists. In that hypothetical world, the ongoing economic and cultural exchange would have propelled the island towards a different political system. Instead, we doubled down on an approach that has failed for 70+ years.
> the ongoing economic and cultural exchange would have propelled the island towards a different political system
The blocker to this has always been the government refusing to reform. I don't see how increased exchange changes this. If anything, the Cuban government would've blocked any integration that threatens their control.
> we doubled down on an approach that has failed for 70+ years.
I assume by "we", you mean the Cuban leaders who have clung to power and their repressive ways against the best interests of the population?
In that same world we have Puerto Rico with a fragile power grid. I'm not sure what the best course of action is for Puerto Rico, I am from the Island, and there's just way too many issues on the island, the biggest thing I do know is that the old tax incentives made the island thrive drastically. There was a point in time where Puerto Rico was as high up in terms of production quality as Japan, above the US itself. A lot of pharmaceuticals come from Puerto Rico, so much so that hospitals in Florida have shortages if the Island loses power due to a major hurricane.