Guy here retires, did some halfway decent stuff, but not "great" stuff. Duct tape 'n baling wire the whole way 'round. No documentation, and he'd spend half his day off at another site sitting around eating snacks with people instead of getting shit done.

Guess who inherited this and has to untangle it? Oh, and said individual didn't trust "newfangled" technology like DNS, liked to use static IP addresses for everything.