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The Calibre forum is definitely the right place to post the problem in!
I can't help with the first problem except to say that's how I update Calibre on my Mac and, so far, it's always worked fine.
It could be that something's missing, or it could possibly be an issue with your cable. Does the 505 show up in Finder when you connect it with the usb cable? If not, try a different cable.
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