I started with a REB 1100. I really loved that device (especially the backlight and the overall form factor). However, the battery life wasn't very good and putting books on it was ... a pain. When it was upgraded to the 1150 it became a better device, but somehow diminished the reading experience (though I'm not sure I can say why). I used my Sony Clie UX for a while. The downside was the screen size and battery life. The upside was that eReader was nice to use and had a autoscroll that worked very well when I wanted to read while working out.
I leaped to buy the Sony 500 when it came out. I loved that device, though I had to admit that the screen was dimmer than I would have liked. I upgraded to the Sony 505 (with the lightwedge cover) and was in reader heaven for about 2 years. I still think it was one of the best devices made. The lack of connectivity didn't bother me, but I did wish that it had a dictionary.
I've also owned a Kindle 1. I never thought much of it. I found its menu system very frustrating and the lack of page numbers are real downer. (My wife has a Kindle 3 and loves it; my daughter has a Sony 300 and she likes it, but doesn't love it...).
I've switched to the iPad. It is heavier and harder to read in bright sun. But in all other respects, it is a much better reading experience. I like the color. I like the screen size. I love the dictionary. It is easy to get books onto the device (even if I don't buy them through Apple).
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