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.)?
Mostly nothing, except for Home Assistant, which seems to shit the bed every few months. My other services are Docker containers or Proxmox LXCs that just work.