I bought my PRS-500 off of a friend who got it free with her laptop. Since I only paid $50 for it, I'm not too inclined to upgrade to the 505 right now.
I've gotten to play with a 505 in a store, and the only things about it that attract me is the ePub format (which is nice, but not necessary. Calibre converts the files for me), and PDF Re-Flow (no one seems to have nailed disassembly of PDFs quite right).
What would get me to upgrade is if Sony made a new model that had OS X support. Right now, I'm syncing my PRS-500 with Calibre on my Mac, and booting up Windows in VMWare to download ePub books from Google or the Store. That's rather annoying, but I don't do it too often, and frequently the same content is on Project Gutenberg anyway.
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