My dad was part of the forces defending Guam during a war with North Korea. Apparently, they succeeded.

The article is interesting, but it lumps together the territories in a way that isn't super helpful for understanding their individual dynamics. They all happen to be made up of islands, but otherwise these are very different kinds of places! Puerto Rico in particular is way, way bigger than all the rest combined and is more comparable to a US state or a small independent country in size and social complexity, whereas the rest are more like various kinds of old-school colonial possessions.

DC would also like a word or two, and those words are "Senators" and "Representative."

American Samoa has a specific issue where they think citizenship would interact with the traditional system of landownership in a way that would bring it to an end, but that's just Samoa, not territories in general.

Yeah, Puerto Rico should either be a country or a state, and should just take a binding vote. It's way less clear what should happen with the others. For small islands it seems like some association with a larger country works reasonably well and is reasonably popular.

The trouble is Puerto Rico has substantial numbers of people for the status quo, statehood, and independence (and possibly also some sort of status in between that may in fact be snake oil for "all the benefits and none of the drawbacks) so they really suffer from our collective political inability to just put up a ranked-choice referendum with more than two options.

Ranked choice voting is so great. Is there anything it can't solve?

What if we offered them independence plus they could have Florida?