How to sync with iTunes acting as an iPOD

Is it possible, and what is the best / best free way to sync iTunes to an Android device, having all the music transferred that would be transferred to an iPod? Is it possible to have more transferred? ---------------------------------------- The main purpose is to transport the files from a mac to a windows machine so we can process it there, playing experience on the device is secondary. We have music from many sources, in many formats, inside/outside of the library folder. Some are not stored but streamed from the Internet when we play them. (When we try to burn CD's, or export with some app, typically only a few files are exported)