Puerto Rico doesn't make much sense to me - they should either be a state and have the full rights and federal oversight that every other state does, or be their own thing entirely. Living in this limbo world where you're a citizen but sometimes in name only if you're on the island seems wrong.

They’re in a limbo because they don’t agree on what should happen. In the most recent real referendum (2012), a plurality slightly short of a majority wanted to maintain the status quo. But the rest were split: some wanted statehood, but the others wanted to be independent.

Note that Puerto Ricans are fully citizens. The island itself doesn’t have representation in Congress because it’s not a state. (Which is a legal thing that’s distinct from the people who live in the state! The “United States” isn’t just a name, it has legal significance.)

I agree for the historical reasons, but I don't think it should be left to Puerto Rico if they can't decide. The US should just say we are (state-hooding/evicting) you, unless you decide one way or the other. Along those same lines, I also think DC should gain representation in congress in some manner, either by largely becoming part of VA, or by becoming a 51st state(DC has more people than Wyoming or Vermont, and about as much as Alaska).