They are purposefully iconoclast with whatever aesthetics are "socially acceptable" for mainstream nerds. For example, their use of comic-sans in official presentations. Here they use ridiculous slop in front of an audience of conservative unix hackers. You can find it funny with the right mindset.
The upgrade mechanism from 7.9 to 8.0 is still gloriously simple, and exactly the same as it has been for many years :
ssh myopenbsdbox # log-in to your machine
doas sysupgrade # will log you out, go drink some coffee
ssh myopenbsdbox # log-in to the upgraded machine
doas sysmerge # (optional) solve merge conflicts of your cfg files
doas pkg_add -u # (optional) upgrade local packages