To Symbios you listen. Save you from the Dark Side he can :-)
I don't use Winamp but almost all music manager/mp3 loaders usually
support devices which are Mass Storage Device (MSD) compliant. I think
when you even hook up a new USB key device Windows will say "Windows
has detected a new mass-storage device". Most modern MP3 (like
the iLo, Rio Forge players are mass storage device compatiable drives.
Someone told me that even the iPod is mass storage device compatible
but only if you don't install iTunes.
Many older MP3 players like the Rio Karma and early Creative models
aren't mass storage device compatible. Some like the Rio actually had
their devices setup like databases which cut the indexing time at
startup. Most of the other reasons where issues of cost (Micro$oft now
charges MP3 players for use of the FAT file system necessary for MSD
compliance), age of device (some makers didn't think it was an imporant
device feature early one) and DRM issues (Sony still uses this as
justification for not making thier devices MSD compliant).