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So it seems that the Droid doesn't play audio out via usb, would creating an application to fix that be possible? Or is it something that Motorola only would be able to fix?
Yes, I have done it. You do not need a special software. Just connect the Droid to your laptop via usb cable, do not mount it, start up Pandora and it should play through your laptop speakers...
I have tried with my car stereo and it doesn't find any music, even though I have a folder with over 8gb of music. I have tried pandora and that also doesn't work.