The difference is whether the criticism is warranted. Puerto Rico is undeniably not in a good spot and the joke was taking a shot at that.

If someone makes a baseless joke then they aren't worth the time of day, I agree with that.

To expand on the hypothetical question: Japan has a literal garbage island (it's an artificial island used as a landfill). We call it Dream Island (Yume no Shima) because of the irony.

Further reading: https://en.wikipedia.org/wiki/Yumenoshima