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I find that using calibre on a Mac with Sony 505 works really well for me, but then I prefer to buy books where I can strip the DRM in the first place, and I'm not really concerned with buying books in formats that work directly. Plus, I'm in Europe, so access to the Sony store or Amazon.com is not relevant for me. I can't see from your list whether this is an issue.
I generally like the software on the Sony, it's easy to use. Lrf works fine as my format of choice with standard settings, and if you convert in calibre, you can set the base font size to the size you prefer. The only annoying thing is that calibre can't paginate so that will happen on the Reader the first time you open a file. For a long book that can take over 10 min.
I've had to use Windows in VMWare a few times to update firmware and such, but not for getting books on the device, so it hasn't been a problem.
The collections on the Sony works fine for me - I actually prefer it over folders because I can tag one book with more tags. I don't have more than up to 100 book son the Reader - if you want to carry your entire collection, real folder support might be an issue.
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