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.)?
Typically, very little. I have ~40 containers in my Docker stack and by in large it just works. I upgrade stuff here and there as needed. I am getting ready to do a hardware refresh but again with Docker that’s pretty painless.
Most of the time spent in my lab is trying out new things. I’ll find a new something that looks cool and go down the rabbit hole with it for a while. Then back to the status quo.