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(and some good headphones)
i don't think it's an issue with the headphones, although what exactly is this amp you speak of? is it portable?
are you sure that would increase volume as opposed to making everything clearer? i'm not in any doubt that lack of volume is the problem here. as well they look pretty expensive so i'd want to be sure they'd solve the problem.
so it amplifys the sound
the reason it seems so quiet with the Sennheisers *as it did with my HD595s* is that they are underpowered, a portable headphone amp will sort that right out as the power given out by the ipod isn't enough to drive the headphones to their best capacity.
high ohmage phones are tough to drive from an iPod. A headphone amp sounds like what you need
i'm no great expert, but apparently Fiio is a good entry level brand