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well, when i first read your post... i thought it was some lofty dream by someone who didn't have a clue. but i think maybe you might have something here... however, there are 2 major issues:
1. hack the ipod... i'm not sure about this one, but are ipod hd's specially coded like xbox hd? they may be protected so that they can only be used with an ipod... and also the other way around --does the ipod hardware require a coded hd? if so, the super big hd you are adding in there may not work with the ipod interface.
2. how do you connect the hard drive to the ipod and to the laptop computer at the same time? you can't have two devices controlling one drive.
so, i guess the first thing to do is buy ipods with bunk hd's off of ebay ($60 or so) and try to verify it works with non-oe hd's. secondly, the interface problem... you may have to design some kind of ipod emulation program, and design a special piece of hardware to take the ipod cable and have it communicate with your laptop through that emulation software. OR you can have some kind of crazy switching hdd controller to load songs, then switch back to use the ipod controller... but then that's not any better than just putting a wifi enabled laptop in your car and just using itunes to load the ipod the normal way. and a laptop is a lot heavier than an ipod... so maybe you should just disconnect the ipod and bring it inside to load.
okay, so maybe this might be more complicated than i initially thought... good luck if you really want to try this, but i think the costs will end up far outweighing the benefit.
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