Sir,

Winamp has built-in iPod support. Iyon ang gamit ko dahil mas simple ang user interface. Hind siya restrictive kagaya ng iTunes, so you can plug other iPods to the same PC.
Once you plug in your iPod, it automatically appears in the Media Library of Winamp.
Pwede kayo kumopya ng songs from PC to iPod, or iPod to PC.
Album art and photo upload are also supported.

Good luck!