Before 1959 in Cuba literacy was 60-76%, by 1961 it was 96%, Cuba's literacy rate now 99.8%. That's really not that bad. Sure, sure, we know about the camps for homosexuals, him unloading his prisons into Florida, suppression of political parties, etc. etc., but let's take a look at one other thing in Cuba: housing. I'm not really going to touch healthcare beyond this because Cuba is actually very renown for having great healthcare and actually one of the best optometry programs. Moreover, Cuba has traded doctors to other Latin American countries for resources, pretty interesting. Home ownership in Cuba is at 85%, here in the US 66%. Housing conditions were considered very "poor" prior to the revolution at bad conditions 47% of households to after the revolution, 13% (Harvard). Then as Padawanbater pointed out, there's also that one part that you missed. It's not perfect, but it did work, there are ways we could try to implement some of these (education) and maybe we could get out ahead.
We also have this weird mentality that homeless people sometimes deserve to be homeless, whereas in Cuba homeless people deserve to have a home.