I can't really speak with the authority of those who have had both, since I only just got a 500 and haven't ever seen a 505 in person, but I'm going to argue for arguments sake that a replacement 500 might be the better option.
Since Tom Swift has owned a 500 before and has been fine with it, and there is such a price difference, it might make sense to go back to something that Tom Swift already knows and likes, and save the $150 that he would have spent. There are a lot of ebook readers coming out in the next few months, and there is a likelihood that we'll see a Kindle II by x-mas this year. And even if we don't, the number of 505 owners who will be switching to Kindle and dumping their 505 will increase by post-xmas. In other words, if Tom Swift can just manage with what he's got for another 6 months, he'll be $150 closer to a third-gen ebook reader.
That's the reason I decided to get a 500 for myself.
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