The people didn't starve under the US-backed dictatorships, so those regimes have that much going for them. But they didn't starve under Castro either, and living conditions were probably better under Castro than in any country in the Warsaw Pact (see Anthony Daniels' _Utopias Elsewhere_); so I'd guess that most of the story is that Chavez was just that dumb.
An Island like Cuba is just small enough to make actual communism possibly work - it has just slightly less people that the Los Angeles Metro area does - it also has a very homogeneous cultural background. Cuba however isn't quite rich enough in natural resources to actually reach autarky however, if it was, Cuba might be a very different story.
I'm not a proponent of anything Authoritarian, but communism on a small scale does fascinate me.
just small enough to make actual communism possibly work
This is an important distinction. Humans evolved in tribes, and many of our instinctual responses to how we think we should work together are optimized for such a setting. But these things just can't scale upwards. There are many things that work well at a community level that fall apart with larger groups. So when we see a problem in the world and feel our heart-strings tugged, we should be suspicious that our emotional response is something that can really make sense in the big picture.
I do agree that such things might be able to work at small scales. But I suspect that the threshold is well below the size that you're citing here.
I suspect the threshold is actually about 450 people - but if you scale that up, and have multiple units of 450 people each - then you start to have something workable. The long term problem with planned economies is the inherent inflexibility and immovability in the face of changing realities.
Markets work because they are irrational, and move with people as situations change - like a subconscious reflex - planned economies require conscious effort to reapportion their efforts in the face of change.
The solution to socialism is collectives - lots of little ones from 50-500 people, which then interact with each other using market settlement and price adjustment mechanisms.
