So, after a week of penitence, I made some progress but ultimately hit a wall.
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All the details referred above are still in play.
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After going above and beyond with debugging, turns out that the issue was the following: When I created the new Droplet I used the opportunity to update a few things I wasn’t able to do back then with the original one. One of those was IPv6. Turns out that Digital Ocean’s IPv6 Ranges are mostly banned by Google for some cosmic reason. So, word of advice to the future: If you are setting up a DO Discourse Installation, don’t set up IPv6, because you can’t remove that IPv6 later, you will have to change Droplet.
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After correcting that, everything worked as expected. However, due to normal growth (and some recent tactics by Alphabet) I’m back to square zero because now I get this error and I don’t know of any way to “stop” Discourse from processing oneboxes (I even tried adding the YT domain to the Blacklist, with no success). This is because according to that post I linked “it should go away after an hour”, but I can’t freeze my rebakes… or can I? Should I? The other options rely on changing stuff on the server’s side but that would be… adding more IPs? Forcing “X-Forwarded-For” on Onebox calls?
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Also, a bonus question: Why does Discourse “take the load” of calling YT? I mean, this error suggests that it is the Server’s IP that is being flagged as doing all the calls (yes, it is because of the onebox unfurl), but… why doesn’t that fall under the user loading the page? Performance?