Something nonobvious about Cory’s past is that he was a Sysadmin at one point. His Sysadmin characters, I’m sure, are an amalgam of the many of us he’s gotten to know over the years. He spent quite a bit of time in that culture, including the first dot-com bubble, so IMHO, I’ve always assumed his chars from the sysadmin/perspective were derived from that experience.
for me personally, I’ve always identified strongly with MonkeyBagels’ Origins of Sysadmins document.