Keep in mind the original price for Kindle 1 was $399 before it dropped to $359. As much as I wanted one, it was still too pricey for me.
I had mentally pegged a ballpark price of $200 in mind before I would buy an eReader. (I didn't realize that I would save money over what I was spending in p-books...I just saw it as a cool gadget for an avid reader). However, when they had the Chase credit card offer, I figured if I wanted one in the near future, I better buy at $259. I am so glad I did.
I bought my mother's Kindle on the Oprah deal primarily because I missed sharing books with her. But unlike me, she wasn't looking for one and as much as I love my Kindle, I think I would've waited if it weren't for the discount as much as I now realize the benefits of owning one.
So if I wasn't able to justify spending that much on my first Kindle, I think I would have a much harder time spending that amount on an upgrade...of course, that's easier to say when there isn't something out to tempt me