I normally don't use the Sony S/W because I had my 505 before they supported the Mac (or anywhere outside the US)... I found Calibre and have been using that virtually since its inception.
Calibre meets all my needs unless I wish to buy a DRM encoded book... something I rarely do as I am opposed to DRM... it basically says I don't trust customers and usually interferes with a customer's ease of product use. If Baen can make non-DRM work then others could as well.
Having said that, when Sony finally deigned to support the Mac, I found the software easy to install and easy to use (tho' it helps to take a few minutes reading about it) but already had ADE installed anyway. Can't remember last time I used Sony S/W once I disabled auto-start when connecting reader :-)
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