I am a soldier, so I had most of the same concerns he has. The big problem these days is that we are not allowed to connect USB devices to government computers. That includes readers, so downloading on a government computer is out. Internet access for personal computers really depends on where you go. In my experience, it ranges from free in Kandahar to available for a fee in Kuwait and Baghdad to non-existent in Basra. The more remote the location, the less likely that personal internet will be available. Given that, he shouldn't expect to be able to download during the deployment.
A reader that supports flash memory cards is handy because his family can periodically mail him an SD card loaded with books, pictures, etc for him. It's also possible to mail a CD, but that requires him to have a personal laptop. I'm not sure how well that would work with DRMed books. I know for certain that I can load DRMed ePubs on my SD card and then read them on my PP.
Smaller is better than larger. The 5" size fits in pockets while the 6" does not. Packing space is tight and downrange it's difficult to carry a bag during the day since they aren't allowed in the dining facilities etc. If I can fit it in a pocket, I can have it available more.
A zipper case is mandatory for this sort of lifestyle. There are too many sharp bits in our luggage and the sand is too thick. I personally like a a rubberized coating because it hides dirt and fingerprints so well.
Given all of the above, I went with the Astak PocketPro. Compared to the Sony Pocket, its processor is twice as fast, it has an SD card slot, it does text to speech when I can't have a light (not well, but handy when I'm almost at who done it), and it comes with everything I need in the box, including a 2GB SD card. You get all of this for the same price as the Sony, which doesn't have an SD card slot or text to speech. Also, the Sony needs a different cord to charge it from a wall socket. While both have batteries that will last half of forever, finding time to leave you reader plugged into your own computer while it's running for long enough to charge it can be difficult. The PP comes with a USB wall plug and USB cable, so I could charge it from a wall outlet right out of the box.
The CaseLogic zipper case for the Sony Pocket fits the PP perfectly. BookArmor also has a new case that is designed to leave a lot of space around the reader and might fit some readers that are a little wider than the Sony and PP.
Most devices are designed to be sold globally and support multiple languages. The PP is distributed by LBook in eastern Europe, so there's even Russian firmware available for it. I would imagine that the Sony Pocket has similar support but don't know that for certain.
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