A friend asked for advice on Facebook about using free software to manage an iPod that works on both Windows and Mac that is NOT iTunes. This has come up repeatedly over the years, even though I didn't have much specific relevant information, I'd searched for it before. And I was curious myself.
Between web searches, and a list of software that he was recommended, I came up with a list. From that list, a clear first choice emerged.
I'm recommending that he try Songbird.
floola - Mac, Windows, reads like what he wants. I installed it in Windows 7 and it discovered my music in seconds.
yamipod - a different twist on this category. The software installs on your iPod and you execute it from there when it is plugged into your computer. Says it works with Windows, Mac and Linux
Songbird - Windows and Mac, very mature product. I had to dig, but this page states they support his iPod SongBird Device Support