The same argument could be applied to all of my examples, I think they all have people who argue that their current states are worse than they could be. That's why I defined "working" as "functioning" not "as good as it could be," or even "well-managed."
In a world with (and a history of) many countries full of mass starvation and homelessness, my definition of functioning is anything above mass starvation and homelessness.
No, that's absolutely incomparable. Cuba is a shithole from hell comparable only to places such as North Korea, Bolivia or Venezuela (coincidentally also socialist states, huh), none of the other places are.