Hmm -- if someone threw that comment at my direction, I'd just assume they were a complete idiot, and not worth a further second of my time. I certainly wouldn't take it as a cue that I need to "man up", or that I should vote for whatever party they were shilling for.
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.
But hey, that's just me.