Let me give a shoot-in-the-dark estimation: maybe this coming holiday shopping season? I think it makes sense to do a yearly update -- Just like what sony did with PRS series.
I wouldn't worry that much about kindle resell value. There were some faults with Kindle 1, like huge buttons (I actually enjoy it personally). The majority of them, however, were software issues. Given Amazon's business model on content, I think we will get firmware update even when K2 comes out.
On the other hand, it seemed that Sony had abandoned PRS500 users altogether. I am not surprised -- Sony is such a nasty HARDWARE manufacture and all they want you to do is to upgrade to the latest models. Yuk...
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