Since MacWorld is just around the corner I don’t have much wiggleroom on my speculation, so I’m going to hedge a bit on my conclusion that a $100 iPod is a way off: A super-aggressive price on a low-end HDD-based iPod from Apple would be an interesting shot at the likes of Dell. I’d guess it would take Apple’s competitors at least 3 months to respond at that price point and might set their efforts in that space back another 6-9 months. If my SWAG is accurate, such a move could be worth Apple’s while.
In anycase, the more I think about it, the more I expect that Apple will start bundling a significant number of tracks from iTMS with any low-end iPod. This approach was used in the early day of the market for compact disks and CD players (though I don’t know how successfully), and would be a smart way for Apple to compete on hardware prices while both keeping their average transaction price up AND promoting iTMS.