You're pretty far off as far as Cuba is concerned. Last time I was in Cuba was 17 years ago (through Canada). I don't think a lot has changed....
- Maybe lots of public spaces, hard to know. Not much commerce going on so lots of empty spaces in cities with people hanging around. If that's your idea of Parks and Recreation, fine. Seemed pretty dull and depressing unless you were looking for an underaged prostitute.
- Yeah, you only have one oppressor, Fidel & Company. But you don't have any functional legal protections. None whatsoever. The party says you're toast and you are indeed toast (if there was any toast around). Actually, the one oppressor rule wasn't quite correct. There is a thriving black market and those sorts of things are not run by idealistic people. I will leave you to figure out the details. It's not hard.
- Culture? Depends on your definition, I suppose. What I saw was mostly a wide varieties of different folk cultures. Interesting, but probably cost a couple of thousand dollars across the entire island.
- City planning? Without much money, the only planning you get is what was there before the economy tanked and the relentless creativeness of humans. The only central planning that sort of worked was with agriculture and that carried a high price (not everybody likes to be forced into farming). Castro's planning failures are legion.
Yes, you can argue that Cuba hasn't devolved into the horrid mess that is Haiti and the slow motion train wreck that is Puerto Rico and to a large extent the Castro's are responsible for that. But we all know that dictatorship is probably the most efficient of human political arrangements. It just lacks a few things.