iPod troubles

[yoh]

So yesterday, fed up with half my music not working on my iPod for some odd reason, I decided "You know what?, I'm going to delete my music from my iPod and re-sync it with Winamp" Since then the music has not been showing on my iPod nor through Winamp, and before anyone asks Yes, I did use the iPod update to fix syncing issues, but it hasn't helped, I've had to run the patch each time to get anything onto it. Each time after I disconnect my iPod and plug it back in to put more on? It's not there. I've had to go to the iPod folder and manually delete it all.

Please tell me what I'm doing wrong here.

Oh and for the Record, I'm using an iPod classic 160GB.