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You definitely could do that to my recollection, I remember doing so to ferry files around.

Here's an apple support doc showing how:

This was not a viable option pre 6th gen.

It was if you ran ipodlinux instead of the stock OS!

I had forgotten about this, thanks for the reminder :)

From firsthand experience? I think my 2003 iPod w/ Dock Connector can still boot to Disk Mode.