Why not compare it to the DR? Neighbor right next door with similar demographics to Cuba but closer economic and political system to that of the US.

Not doubt the embargo has done some damage to the wellbeing of the island, but the self imposed economic system makes things far worse.

Sure. But why only DR? We also have Jamaica and Haiti near Cuba.

The Human Development Index:

Dominican Republic: 0,776 Cuba: 0,762 Jamaica: 0,720 Haiti: 0,554

Only Cuba is socialist. The other three are capitalist. Considering that Cuba suffers from sanctions, like Haiti, it is impressive how they managed to achieve an HDI almost as high as the DR, a value considerably higher than the average in the Caribbean.