My server was up for 3.5 years with no outages because I just didn't touch it.

Problem #1 keeping OS current. Chances are you run an outdated OS with some RCE vulnerabilities.

Problem #2 setup is hard to scale organizationally. How to give access to the server to other people? How to monitor what they do? How to replicate server setup across teams and keep it in sync? So on and so forth.

In an org. something always change, and you have to touch servers as a result.