Like I said: Compared to Haiti, or Venezuela, or Panama, or Simbabwe, or Ruanda, they did pretty well. Depending on the point in time over the last 50 years and your position in society, even Mexico (Drug wars, now), Argentina (during the dictatorship), or Brasil (born into the wrong class, today) may not be clearly superior in every regard.
I've been to Cuba, and life there is somewhat boring, and the standard of living is obviously low. But it's not the kind of poverty you seen many other countries. No starving old people and children in the streets, also no gang violence ruling your block.
Streetlife in general seemed quite happy – old people playing chess, young girls playing soccer (in school uniforms, no less), groups of three or four neighbors fixing one of those old cars etc.
Now it sounds too much like glorification – I also listened to 6 hours of Castro's labor day sermon in 2003 and most people around me felt I was insane for attending it voluntarily – they only went because somebody, somewhere had to check their name of a list or they may get into trouble. That's a price I wouldn't be willing to pay.
I hope Cuba will find a way to preserve a bit of what made it bearable in its worst times.
Why not compare to the Dominican Republic, say? That seems like a much closer comparison in so many ways - capitalism under a ruthless dictator, a long history of US intervention etc.