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.)?
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Generally, no. Most of the time the updates work without a hitch. The the exception of Nextcloud, which will always break during an upgrade.
And why I no longer run NC. Every time it would fuck itself to death and I’d have to start from scratch again.