I think the key is getting the right device for the person. There are very tech savy seniors, see fredlave, and then there is my Mother. She does fine with a computer and her DXG but has never bothered to learn how to use collections or remove books from the device. I take care of removing books for her when I visit. It makes everyones life easier. My Dad tries to understand and gets frustrated that he does not.
And then there is me. I use tech but I am not tech savy. I have never hacked anything, nor do I want to try. When my computer crashed, I let the hubby deal with it. But I can use an IPad and a Kindle just fine and figure out a few tricks here or there.
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