Selfhosted
A place to share alternatives to popular online services that can be self-hosted without giving up privacy or locking you into a service you don't control.
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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.
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.