I've only witnessed it on the sidelines (while the internationally distributed company I worked for was acquired).
> It's a giant headache that can never be properly fixed, yet v6 completely avoids it.
It's a headache, sure. But that it can't be fixed is hyperbole. All it takes is reassignment of IP addresses, there are plenty after all. The headache comes only from IP addresses stored in places they don't belong. If they were only stored in the DHCP and DNS servers, a script could fix this in no time. Part of the problem I witnessed was, that people are hesitant to use DHCP for static IP addresses (servers) and some devices (switches) are incapable of using DHCP.
I also observed (much earlier) misguided sysadmins using a scheme encoding location of a device in its name. That of course let to horrible long, unpronounceable names and people remembering and using rather its IP address (that danger of course is greatly reduced with IPv6 ;-}