Derogatory? The facts are simple, it is a war prize, nothing more and nothing less.
The US forcibly took possession of PR
from Spain in the Spanish American war. That Spain had "discovered" "conquered" "subjugated" or whatever you want to call it previously, has no bearing on the fact that the US took possession of PR
as a prize of war.
Now, as to whether the continuing status as an insular possession is derogatory...I can't tell you. If anyone in PR
feels defamed by that status, they can get up and vote for Statehood and take all that brings. But apparently a majority of Puertoricanos feel that it is to their advantage to be less than a State. Or, someone keeps casting the votes that way.
Meanwhile, it remains a war prize, and the concepts of independence and freedom, however illusory, don't seem to be the ones valued most there. Go for statehood. Go for nationhood and independence. But, to stay in limbo as a war prize?
That's a concious choice, by the folks who live there.
Chicago, DC, and N'Orleans oughtn't to be lumped into the same bucket as each other, fwiw. DC has a truly unique status, of being a city without a state. Three towns, each with some unique attributes.