WANQer can watch any folder(s) or drive(s) on your system and will automatically keep your playlist updated as files are add, removed, or renamed. Even works with CDROM drives and will update the playlist as discs are inserted and removed.
This works very well for those who are constantly adding new mp3's to their collection. You can watch multiple directories for any change in terms of files added or files removed; and WANQer will then enque or unenque files from your Winamp playlist accordingly.