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I think the 505 is what you're looking for. Sturdy (although all ebook readers fall into the "somewhat fragile" category) and simple; reads books & not much else. (I understand it has an MP3 player, and maybe someday I'll figure out the settings for that.) It has cool hacks; I don't know anything about them, either.
Calibre's open source software allows for conversion from a lot of ebook types; Sony has more range of content (although Kindle has more, and cheaper, access to currently-popular content). The Sony's PDF support is a bit troublesome sometimes (ah, the joys of reading a letter-sized page on a six-inch screen), but the reflow works fine for well-made PDFs. Kindle's PDF support is awful--if the original is well-made, it'll transfer across okay (Amazon has to do the transfer, though, through email or download); if it's weirdly-formatted or badly-made, the results can be unreadable.
Sony has DRM'd epub/PDF support, so you can check out library ebooks with it. (This is the one feature that bumps it away from Aztak's EZ Reader... which has other benefits that I'm a bit blurry about.)
I recently broke the substrate on my PRS-505; Sony's customer service repaired it for the $29 labor fee--if I'd bought insurance, it would've been a free repair. I have no idea what Amazon's break/return policy is.
The grey tones won't matter a bit for text; they only come into play when you're looking at pictures. If you're planning on looking at a lot of image-heavy content, you may consider the difference; if your images are limited to the occasional photo in a newspaper article, or simple bar graphs, the 8-vs-16 shades won't matter. (Even for heavy images, it may not; the dithering tech is good enough to not matter to most people.)
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