Upgrade cycles are a given in tech. However, convincing the accountants to loosen the purse strings for those upgrades is not. Why spend money if it still works? For example, an IT contractor responds to a network problem and discovers how bad the site's cost-cutting measures are: No on-premise IT staff and a server room so sloppy that the source of the problem takes days to find.
Maintaining old tech is always an adventure, but at least it's not another average day at the office.