The standard distribution of Winamp already comes with basic functionalities for connecting iPod/iPhone devices. However, these features are really basic! Album art, smart playlists and ratings are not transferred.
The plugin ‘ml_ipod‘ enables such features (installation and configuration are self-explanatory). Compatibility should be checked with your device at the ml_ipod website, since Apple is not very happy with third party software.
It took me a long while to find a decent alternative for iTunes. First of all I wanted to get rid of Quicktime. It’s a player that really likes to hijack file associations. Still, I managed to live with that. Unfortunately the iTunes software keeps getting bigger with no benefit whatsoever. In my case I just need a mediaplayer (music player) for Windows that manages a music library and makes it easy to synchronize with my iPod Classic. I don’t need any other software stuffed down my throat containing drivers, connectors, features, ads,… for Apple hardware which I’m not planning to buy!