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After many hours of research I came to a single conclusion: as of today there is no way to upload/download music from iTunes into a Sony NetMD Walkman (via USB).

There are methods to record using line-in/out, but try doing that on an iMac (800mhz FP).

There is a program that will allow a Mac computer to edit/play music from a NetMD device, and this is found here: http://www.sorted.org/~pete/Xmd/

Please feel free to add your thoughts and knowledge.
 

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You are correct in your conclusion. I too tried using a Net MD player and returned it for a refund after several days of searching for a way to move MP3s and recorded data to and from the player. The root of the problem is the digital rights management safeguards that Sony has (foolishly) implemented across the NetMD line.

I posted something about this on ehMac a while ago and I'll reiterate my verdict for you now: the NetMD players are crippleware and are sad proof of what happens when you let lawyers design a product.

It's really too bad, because the minidisc still can't be beat as far as voice-recording capabilities are concerned (a lot of the guys at CBC Radio still use these as their principal news gathering tool). That said, you can mark my words on this: once Apple releases a voice-recording enabled iPod, Sony's minidisk is toast.

By the way, I am told that the earlier models don't have the same digital rights management features...so you might be able to snag one from eBay.
 

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I am facing the same problem. I am planning to try running Virtual PC and using the Sony (PC) software that came with the MD recorder. I'm wondering how well this will work. Has anyone tried this?
 
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