Okay, I've discovered the problem -I'm an idiot.
All of the documents I have in the Personal Documents storage were on my device at the time. That's why the Documents menu was greyed out -there was nothing to download until they weren't on the device.
With the cost of 3g being a $60 premium plus $0.99/MB, it's pretty pricey though. Especially when I'm going to have an iPad with me, and can pack the Kobo Mini as a pocket option. And the smartphone, of course. I still prefer the Kindle interface to Kobo's, though.
Worth a try to ask. Thanks anyways!
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