If I sync using Wifi, it works GREAT! BUT, when I sync using USB, Winamp thinks it's a different phone and syncs it in an entirely different way (tracks get deleted, etc.).
WinAmp tries to use ID3 tags to rename (!) your files -- sounds like exactly why I moved away from iTunes... Anyways, make sure that after you are sync'ed, preferences under:
Options - Preferences --> Media Library --> Portables
Options - Preferences --> Media Library --> Portables --> DeviceID
Options - Preferences --> Media Library --> CD Ripping
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