It took a year and a few months, but after starting my project to listen to every song on my Ipod at least once last year, I finally did it! 5212 songs.
It should really have been sooner - I used to listen to music for about 5-6 hours a day (or more) while I worked - but the last couple of years, my calendar has been littered with meetings making it impossible to listen to my Ipod while working. In any case, I made some significant progress on it recently. When I saw that I had about 200 songs left, things started moving more quickly and I now find myself completing this strange and very obsessive-compulsive project LOL. (I mean, there is no real purpose in listening to all songs in my Ipod right? hehe) Nevertheless, I can now finally start adding new songs to my library. About time! :)