I recognize this will vary depending on how much you self-host, so I’m curious about the range of experiences from the few self-hosted things to the many self-hosted things.
Also how might you compare it to other maintenance of your other online systems (e.g. personal computer/phone/etc.)?
I run everything in containers that rebuild every time / auto update but I do so because I have everything backed up and I can easily roll back if something doesn’t work. I mount storage separately so I can simply remount an older backup to the same place in the file system.
Took a good day to set it all up but now I can add anything else I need with a simple compose script. The main host is also built from an image that auto updates every night.
So basically I spend zero time anymore bar when XZ happened since I use a rolling release (yes, I’m a mad man but I enjoy the odd breakage to see what’s going on in the Linux world).
The real trick is partitioning the OS up so that boot image and system are on an SSD and everything else on a massive RAID array with snapshots written to the array and all scripts/configs in git. It means I can rebuild the entire setup in a matter of minutes.