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It seems that the optimal solution would be to obtain a modern device with removable media. I wish Apple hadn't decided to make storage size part of their pricing model, and offered a card slot.

My Motorola Droid phone has a micro SD slot, with a max size of 64 GB. It would be a lot more convenient to carry a phone and 6 memory cards than a phone and an iPod Classic.

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Sansa Clip+ also uses micro SD cards. That being said I used to have most of my music around with me all the time, but there was no point in that. It just degraded into this: http://i.imgur.com/p8Egi.png

I bought a Clip and I just load up music now and then that I am currently listening to a lot.

That's a matter of opinion though, I would much rather take the phone and iPod Classic because I do not wish to deal with the memory cards, especially since most Android phones require you to remove the battery to switch cards.

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