I recently purchased a Sansa Clip Zip, and I am looking for a good solution to sync my iTunes library onto it.  Any suggestions?   I am aware that one can simply drag and drop music folders onto a MP3 player as if it were a thumb drive.  In this case, I am looking for something more...

N00b question warning:   In the past, I ran a single cable from my onboard Realtek sound output to a Plantronics headset/speaker switch, which allowed me to use speakers or headset as the circumstance demanded.   However, I recently took my first step towards higher-fi PC gaming audio...