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Originally Posted by kyteflyer
3) How do these two manage books which are not purchased from the dedicated store? Are they "registered" in any way with the respective websites, or ignored.
4) Does anyone think there might be an argument for having both readers? (Seems a bit excessive to me, but then, I am given to excession at times  )
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My first reader was a Kobo Wireless, then I picked up a Kobo Touch (about to get replaced with a Glo) and ultimately a Kindle Touch as well...so I've struggled with this very issue myself, just one generation back.
As far as the reading experience goes, I greatly prefer the Kobo. I like having the cover displayed when the unit's turned off, and I just generally prefer the interface. The one weak spot, where I really have to give the Kindle credit, is store integration in general and wish lists in particular. The Kobo has a rudimentary wish list that's only accessible through the device, but the Kindle can see and easily manipulate your existing wish list(s).
As far as buying from third party bookstores, I much prefer buying EPUBs that will go on my Kobo than MOBIs for my Kindle. First of all, there are simply more EPUB stores, and secondly, I can just put the new books on a microSD stick without having to connect a USB cable. (Or, for DRM-free EPUBs, I can use the Kobo browser and download 'em directly to the internal memory!) Big win for Kobo there.
All in all, I'll let my money speak for me: as noted above, I'm jumping through hoops to buy a new Kobo Glo, despite it being much easier to get a Kindle Paperwhite. The Kobo's where I do the lion's share of my reading; I only got the Kindle so I'd have access to Kindle-only deals and books. (I determined that I'd rather buy the second reader than deal with an ongoing conversion hassle, and I don't regret it.)