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I don't do upgrades (well, not in the sense most people think of them).
My approach is that upgrades are too risky, things always break. It's also why I don't permit auto updates on anything. I'd rather do manual updates than dedicated time. Keeping things working is more important, and I have backups.
I run everything virtualized (as much as I can), so I can test upgrades by cloning a system and upgrading the clone. If that fails, I simply build a new system based on some templates I keep. Run in parallel, copy config and data as best I can, then migrate. Just migrated my Jellyfin setup this way.
This is a common methodology in enterprise, which virtualization makes a lot easier for us self hosters.
I haven't had a disruption from updates/upgrades in 5 years.
It’s not common in enterprise to not auto-update.
Depends on the company and the system. Some of them need to be done off-hours while people aren't using them. Some are HA and/or insignificant enough that you can do them any time without interruption.
I have not had any auto update in my entire career but i have always been on the infra side so it was never just my app. Though I do wish the update/outage process would be updated to reflect kubernetes and not just think of everything as monolithic servers.
It's extremely common...most production lines I've ever been to only do manual updates on equipment, if any at all.
It's also not uncommon in enterprises that things break needlessly.
That's an interesting process... you could improve it with some ansible - if that's your thing... or use snapshots on the VM(s) and roll back?
That's kinda what I'm doing with this (physical obviously) Pi... take a full backup now and again... do upgrades... rollback when completely borked.