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He also said that it should be possible to load iPod songs to the hard drive (which would be a lot quicker than loading cd by cd.
If he finds out how this is all done, I'll pass it on.
I think your dealer doesn't know what he's talking about, well, as in the case of most dealers, including mine. Truth is, the Navi with HDD only records songs from CD-Audio, and encodes it to its own proprietary MP3 format. And any saved MP3s in the HDD cannot be played on regular MP3 players because of its proprietary format, granting you find a way to rip them off the HDD in the first place.
I am more inclined to believe that Navi updates will be CD/DVD based rather than using that jack beneath the navi screen. This is how navteq currently updates their database, and I don't see anything special with the Outlander to deviate from this standard update process.