He's kinda grown up with his audience. I dropped out of watching as I hit adulthood, then tuned back in for his "meme review" phase, where the inside joke was that everyone watching was a nine-year-old, when in reality he already had an aging audience.
He eventually grew bored with the format (and at that point already he made it clear he was doing it for fun, not because he needed to). The view counts steadily trended downwards as he switched to making videos he wanted to make, instead of ones that made money, as he was set by then.
At some point he ran a book-club style format, because he wanted to get into reading more. At least some portion of the fanbase was into that, but at that point he lost a lot of viewership.
Nowadays he seems to post very infrequently, and it seems to mostly be vlog-style content about family life and living in Japan.
You mention timeshift, did you restore to the working snapshot after selecting it in grub, then reboot AGAIN?
Booting a snapshot, does not restore from it. When booting a snapshot from grub, you need to open timeshift, restore the snapshot, then boot up a second time (this time without selecting it in grub).
Otherwise, you didn't really restore it, you just booted into it, and if you re-attempted the broken update, messed the snapshot up, too (leaving you with no working snapshot to go back to).