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I too am a new Sony user -- it took me about one day to decide to switch to Calibre, because inconsistent metadata was driving me crazy. Also, I somehow managed to crash the reader and only the instructions in the troubleshooting forum here saved me (thanks!).
I only use the Sony software when I want to buy books from Sony -- which I sometimes do for convenience of format or because they have the best price.
But I use Calibre -- which is extremely user-friendly -- to actually manage my 505; I just find it way easier.
The only glitch is that it does not pre-paginate the file for you, so that when you first open a book on the reader, if you loaded it using Calibre, the reader will take a minute or three, depending on the size of the file, to paginate the book. It also does this if you change font size in the display -- I usually want large because of vision problems. But only the first time you open it or change sizes; after that, you're good to go ...
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