My personal preference is to use iTunes (doesn't matter wether you're a Windoze or Mac user) because it's supported by LW and it's playlist functions are great.
Plus (I don't know if that's true or not but hey, 'zat's how it lookz to me) it kinda lets LW to do just the dlding/uploading

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iMac G4 OSX 10.3.9
RAM 256MB
LW 4.10.5 Basic
ADSL anything from 3 to 8Mbps/around 1024kbps

"Raise your can of Beer on high
And seal your fate forever
Our best years have passed us by
The Golden Age Of Leather"
-Blue Öyster Cult-