Since this cross-posts to Twitter, word of warning. DigitalOcean's one-click Mastodon setup is still on Ubuntu 18 and like v3.1.x.
I had to upgrade Node to 14 during the process was the main thing. Other than that, and a weird webpack compile issue, smooth sailing.
Screw it; let's tempt fate and do an Ubuntu upgrade tonight. Something something leeroy jenkins?
This did not go well, and I've just spent the last four hours doing manual data recovery from a broken Droplet to a new droplet. That was a painful experience, and I've learned my lesson.
Thanks, DigitalOcean, for pointing me in the right direction. Also, have more money and do automatic backups for me kthx