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Pica does he have someone who can help him? An aide or a friend? If he does then you might find 3G beneficial. You won't have to worry about mailing a memory card to him and he could get new books more regularly.
I would think a Nook Classic would fit the bill. It has the memory card and 3G access so he would have the best of both worlds.
I don't think that the life of the battery is going to be an issue. These batteries are meant to last 3-5 years. By that time you might want to replace the e-reader for a new one. Hopefully larger, lighter models will fall into your price range.
I would think that he would benefit from the DXG or 950. The larger screen would allow for more words on the page, especially in landscape mode. Then again, they might be too heavy and they are out of your price range.
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