I can only speak of my own experience as a sysadmin, but the more isolated the system is and the less critical it is for operation, the easier it is to delegate the job of doing a software update to coworkers and new hire. Especially if all the issues from doing an update has already been established on several other machines, in which case the update is more or less mechanical in nature.

It reminds me of the story about a thirty year old Commodore Amiga running the AC system for a school district. The district finally decided to modernize the AC for $2 million, but until then it was just cheaper and easier to continue paying a person to run it every year. Replacing hardware systems is expensive and political complicated, while continuing paying an employee is just status quo.