Legit question: why buy each version? Is it just for fun, or is it because the new versions have a feature you craved? Or is it because something went wrong with your current version? I have a three year old Kindle and, as far as readers go, it's good. I'm trying to think what would make me upgrade and I'm just not seeing a compelling reason in these new versions. Mostly the new features seem to add things I don't want/care about: touch, GoodReads integration, etc.
I had the very first version. I upgraded to the last version before paperwhite because the screen was much better. I upgraded to paperwhite because I saw the integrated light and it's much comfortable than other solutions (and luminosity was an issue eg in planes on older kindle). I may upgrade to the voyage one because it's smaller and i miss the change page button of the older kindles which this one seems to mimic.
So for me it's not that the one I had at each time was too old, or for fun, but because the new version adds something that genuinely improve my reading comfort, while being cheap enough that I don't need to think much about that expense.
Sounds like my upgrade path. I went launch Kindle (for $400!) to Kindle 3 (before it was renamed to Kindle Keyboard) and then to the Paperwhite.
For me, the reasons went: "new," "screen contrast + first-party lighted case," "built-in light + size" in that order.
I've pre-ordered a Voyage. That's in part because of increased clarity and even thinner form factor, and in part because it frees up my PW for my gf, who honestly uses e-paper Kindles more than I do.
I have a 3 year old kindle as well. I might upgrade to Kindle voyage because of the high PPI. Hopefully they have improved the refresh rate of the display as well. In the older kindles you have to make a choice between refresh every page (slow) or artefacts. I don't know why they didn't make the refresh every n page configurable (6 by default I think)
I bought one model (4th gen I think) because it was much lighter and I noticed my wrist got a bit sore during long reading stretches. I bought the first model with the touchscreen because navigating the store on the device was annoying with the directional keypad thing. I bought the Paperwhite because of the built-in light - I mostly read in bed so this was a big win.
I like having at least one "backup" to lend to family members on vacation. I also bought a cheap waterproof-case (it's essentially a double-sealed Ziploc bag) so I just toss an older model in that and float around the pool and read worry free.
I also like supporting the product line with my wallet - and it's fun to get new toys every year or two :)