I dunno, I suspect a lot of Puerto Ricans will still want some sort of autonomous status even after statehood, which is why I'm a lot more lukewarm/cautious about it than other red avatars. Public opinion seems to be about 50-50 (ok, 52-48) on it, and opponents of statehood feel that way for a reason.
Puerto Rico is the kind of situation which really calls for a Greenland/Aland Islands type solution with significant local autonomy while still being tied to the US state. Something along the lines of US citizenship and federal representation but a lot more power in their finances, laws, etc. Hard to see how that would work given the present derangement of the GOP but that seems the most logical option.
Given that the big desire for PR statehood tends to come from the fact that they have no representation, wouldn't a simple solution be to simply give them representation via constitutional amendment?
It doesn't even need to be full representation they could get say, 1 Senator (as opposed to 2) and half of whichever many House representatives they'd be entitled to.