I've only had two - a Nook Simple Touch and a Kindle Paperwhite 3.
I don't generally replace things that don't need replacing (but sometimes I do - it depends on my mood). So my purchases of competing devices are usually few and far between. Meaning that the technology has advanced so much between purchases that of course, I will like the newer model better. And I do like my Paperwhite better than the Nook. Because it has a backlight that the Nook lacked. Other features - DPI, bezel width, buttons, special software features - I really don't care much about. I will learn to use what I have. Screen size might matter, bigger for better readability, smaller for better portability. So it's not set in stone that my next eReader will be larger. Because I like to carry them around.
I will replace the Paperwhite when it breaks and I need a new eReader. For now, it meets my needs just fine. And I certainly hope that the new model that I eventually buy I will like better than the old model. If not, then that means I made a bad purchase decision. I will research the current eReader offerings when I need a new one, and make a decision at that time.
I consider eReaders a commodity item. All do the same thing, with very little to differentiate between them. I might notice some differences between models, but nothing that greatly affects functionality. The color temperature of the light can be changed? Some think that's very important, but I couldn't care less. As long as it's got a light, my eyes will adjust and adapt to the color temperature of it just fine. But I don't read books for eight hours straight in the dark where things like the specifics of the light might make a difference. I'm more of an incidental reader, I just read whenever I feel like it, sometimes with long pauses between sessions - I don't plan daily sessions and times (but I have friends that do that, so I know it's not unheard of).
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