I carry my 300 in my front pants pocket all the time. It fits great, and is a huge plus for me. The 500/505 were just a little too big for this, and a bit too thin to do this comfortably. I never expected to carry it in a shirt pocket.
I like the current Reader sizes because of the similarity to the size of paperback books (of which I've read thousands) and ability to vary font sizes and still have lots of text on-screen. The freedom from constant charging is alos a huge plus. I could see a smaller screen size (maybe 4"?) but personally would not want much smaller, as font size and/or text per page would suffer.
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