I've been to Cuba twice, two weeks each time, and loved each trip. I found the people to be more open than anyone would think - I've heard a number of very cogent (and unhappy but accepting) explanations of how the current repressive regime has stayed in power. (The best one, and one most frequently heard, revolves around rum and condoms, and I'll leave it there.) No doubt for me that the US and Cuban governments share blame for the falling out but as someone who's traveled to a few dozen countries, I've learned that governments are not always the best expression of the people who are governed. Yes, I've met a few who resented the well sneakered and digitally kitted out tourists, but more frequently I met people who were proud of what they had, and not resentful for what they didn't have.
I've traveled to a lot of tropical countries, and what you see in Cuba's decaying physical infrastructure is perfectly characteristic of what every tropical country would look like if it lacked the capital to do upkeep. Trips through Cambodia, Vietnam, Sri Lanka, even Puerto Rico, will show you that a lot of Cuba's "bombed out" look is simply how mold, rot, and tropical weather take their toll on infrastructure. The phenomenal investments of the Spanish and then the American gambling kings and gangsters built up an infrastructure that is spectacular to look at, but at the same time, costly to maintain. What's unique about Cuba (and Puerto Rico) is the crazy color that underpins the decay. Photographer heaven.
My favorite memory kind of sums it up. Was in one of those lovely franken-car convertibles riding down the Malecon with three other photographers. Two sitting up on the back, one standing, another holding a camera down over the side at almost street level, all shooting away - no one sitting nicely in our seats. Suddenly we're at a traffic light and notice that right in front of us is an old wood-sided truck FULL of police. The driver of our car went into a mild panic - he's supposed to keep his passengers under control. We were panicked - we thought we were in for an unpleasant lecture at best. What happened instead was the truck full of police convulsed with laughter, both at how foolish we looked, and how frightened we looked. And for the remainder of the red light, they posed for us in various ways both threatening and hilariously goofy, and when the light changed, they motioned sternly for us to sit down, and waved goodbye.
People are people. Cubans are poor in material things but rich in spirit, which makes them such wonderful photographic subjects. I've been to many countries rich in material things but poor in spirit, and that makes for poor photography.