The question itself doesn't insinuate anything about independence, true. The thing is however, that a No would have triggered Puerto Rico Senate bill 1467, which states that a 7 member commission would need to be created to negotiate with the US for either a Free Association or Independence for Puerto Rico. The main idea of this vote was to resolve the status of Puerto Rico, one way or another.

Yes won, so Puerto Rico will most probably apply for statehood. But here it gets interesting: Puerto Rico is mostly latinx, which sounds good for the Democrats. But on the other hand, they're fairly right-wing, so it's actually better for Republicans. So, do you think a Democrat like Biden would go forward with the application for statehood, knowing it could cost him the next election?

This is why I say that it's ambiguous: Puerto Rico can apply for statehood, but the process can stay in limbo for a long time due to the political divide. A "No" would have a similar problem; what President would want to have in his resume that he lost some territory? So those negotiations would have stalled indefinitely for sure, too.

I'm not sure you can apply political leanings in PR to the mainland parties. Sure, some might be right leaning and some might be conservative but that doesn't mean they would jump on to the Republicans. Don't forget that Republicans are an extremist party. An extremist party who did everything in their power to not grant them statehood because they hate them. The chance of PR becoming a red state after the democrats granted them statehood is basically zero. No democrat thinks that PR would ever turn red. Any sane democrat will want both PR and DC as a state to clutch the senate forever. Though there hasn't been a chance or much motivation in the past 20 years to do that.

Now is the right time. So I hope the ever stronger progressive side will push hard for it. It doesn't have to happen now, but maybe a nice goal for Biden's second term.

I'll have to dig to find it if you want a link, but when asked about this a couple years ago, Puerto Ricans actually identified somewhat more as Republicans than Democrats.

In fact, most politicians in Puerto Rico are affiliatied with either one or the other. And despite it's name, the New Progressive Party (the party who supports statehood) has about 2/3rd of it's members being Republicans. Their biggest opponent, the Popular Democratic Party is firmly in support of the status quo and dominated by democrats. This males it quite a bit more difficult for the democrats to openly support statehood, as it would be backstabbing their biggest supporting party.

Of course, having a Democrat granting them statehood would make that one pretty certain of getting the vote from PR. But there's no guarantee this boost will last long considering where most democrats in Puerto Rico stand on this question.

Another thing to note is that during the latest house elections, both parties took a heavy hit with 2 new parties emerging and stealing about 15% of the votes right off the bat, and the independence party more than doubling in votes. In other words, the island is very split in this question.

As for DC, you're right that the democrats have a guaranteed vote here. Even Reagan could only get the democrat dominance in that state down to low 80's, and normally it's over 90% Democratic.

One man's best choice is another man's alternative choice.

And try as I like, a small crack appears in my diplomacy-dike.
"By definition", I begin,
"Alternative Medicine", I continue,
"Has either not been proved to work, or been proved not to work.
Do you know what they call 'alternative medicine' that's been proved to work?
Medicine."

 - Tim Minchin

A shame medicine and politics are not wholly comparable... Hell, even medicine is not clear-cut and obvious...

Some best choices are objectively best, but get rejected by people who don't want to be rational.

Sure but the objectively best choice is not always obvious.

Trump enacts last second policy changes before leaving office, removes LGBTQ discrimination protections.

Disgusting human being to the very core. Yeah, I know, Biden will quickly overturn these when he takes office, but it still doesn't make Trump any less of a reprehensible monster. Who'm I kidding? I didn't think it was possible for him to be any more of one, but he keeps setting the bar lower and lower.

There's no place in Hell hot enough for him.

Not for irrational people, yes. Doesn't mean that their choice isn't still very wrong.