I empathize with you, Shawn.
I was running Moodle 1.9, and when I decided to upgrade to version 2, I didn't even try to do it by "upgrading". I thought that it was a good time to start fresh with a Moodle 2.x+ product, and then to restore some of my courses into it. This was two summers ago. In hindsight, I am glad that I did it this way. Enough had changed to warrant a brand new install.
Incidentally, I still have 1.9 installed on my server for the times that I need to reference something from the past.