[mjr00]

Yeah, as someone old enough to have worked at mid-sized companies before cloud-everything became the norm, self-hosting is overly romanticized. People think you'll get a full infrastructure team dedicated to making sure your self-hosted Git/Artifactory/Jira/Grafana/whatever runs super smoothly and never goes down. In reality it ends up being installed by a dev or IT as sort of a side project, and once the config is hacked together (and of course it's a special pet server and not any kind of repeatable infrastructure setup with Ansible or Docker, so yes you're stuck on Ubuntu 12.04 for a decade) they let it "just run" forever because they don't want to touch it (because making changes is the #1 reason for outages) so you're constantly 2+ years behind the latest version of everything.

It's true that outages are probably less frequent, as a consequence of never making any changes, however when something does break e.g. security forces someone to actually upgrade the 5-years-since-end-of-support Ubuntu version and it breaks, it may take several days or weeks to fix because nobody actually knows anything about the configuration because it was last touched 10 years ago by 1 guy who has long left the company.