I was lucky enough to start on the sys admin side and in smaller companies and just after the major switch away from Novell to NT4. I skipped a lot of the early/mid 90s stalwarths.

"client-server" VB6 apps with an MDB file on a NT4 fileshare passing as server is the lowest I've been lucky to have to deal with. Boy that was crap. That and actual cgi-bin script actually written in perl.