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I just got one too, but I probably can answer a few of them:
2. I'm not an expert on iPod devices or anything, but I'd probably have the cause as one of two things:
a. Since you have over 10,000 songs, the 360 might not be able to recognize it all, meaning trying to scan all the files left some of them unread due to overload of resources
b. If any of the songs on your iPod are .acc or are riddled with DRM, then they likely wouldn't be recognized since Apple and Microsoft are rivals and IIRC, the Zune and the iPod do not recognize the proprietary formats of either one (.acc and .wma respectively).
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It'll recognize the AAC files but only if they aren't riddled with DRM, in order for it to read the AAC encoded songs, you need to download an optional update for the iPod's AAC encoded songs to be read. When you download that update, it'll recognize the AAC, WMV, and MP3. I know this because I tried it once with my Nano and it only recognized a small portion of my songs that were mp3 because I never had the update for it to read the aac encoded songs. It's an optional update that's still in the marketplace for download.
Jam it back in, in the dark.