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I think part of the answer has to be the kind of reading experience the person is looking for. Personally, I don't think it is any harder to use the Sony to purchase books as long as the person has rudimentary computer skills. Afterall, it just isn't that hard to download to one's computer and drag from one place to another in order to load books. It just takes a couple of more steps.
More important, I think, is the expected reading experience. For me -- and I'm not suggesting that my preferences dominate and I recognize that happy Kindlers feel otherwise -- I prefer the Sony to the Kindle experience. The Sony is more like reading a pbook whereas the Kindle is more like reading off my laptop. And, yes, I have tried the Kindle. It's not that the reading screens are so different; it is that ergonomics and design, especially the keyboard.
In the end, I think a lot of this has to do with age, experience with computers, and just what one is looking for reading-experience wise. In this case, because the choice appears to be between a Kindle and a Sony, it might be wise to try both and return the less-liked one within the return period.
Just an aside: My parents (who are in their 80s) absolutely refused to even consider the Kindle because of the wireless connection. They were afraid of having their privacy intruded upon by Amazon. I am not suggesting that their fear is rational, but when suggesting a device to someone, it is something to consider. They also refused to join Medic Alert because they didn't want people at Medic Alert to see what medications they are taking. I couldn't convince them (I'm a Medic Alert member) that no one at Medic Alert cares about what medications they take. It's the idea that someone might look, not that someone does.
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