Comment Been here, done it (Score 1) 424
I started as the lone IT administrator for a large commercial insurance company. With almost no documentation, I had to use some RMM tools (Kaseya) and other audit software like Belarc Advisor, and network sniffers to completely figure out everything going on in the company. There were so many terrible band aids, I even had to bring on a few helping hands to help get it done, it took a year. They have 64-bit/32-bit compatibility issues, they had Windows 7 on machines that were trying to run a DOS/Novell shared resource. It was extremely difficult and frustrating, and the pay wasn't as good as easier positions I've been in. However, it was an amazing day when it got completely done.