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Calibre is a great library program. It's not as good for Mac as it is for Linux, but it's good. It's easy to organize things and transfer them, you can get periodicals, and there's a subforum here for it that the creator stops by. It doesn't do audio, but I think you should be able to drag and drop audio files onto your reader. There should be a file with a fairly intuitive name for them, and the samples that came with it will be in there. (Sorry, I don't have the cord with me to check what the file is called.) It will sort them by album, there's no way to get around that that I know of. (Except maybe changing the metadata for each file.)
I haven't heard of any games made for the *50 series, though there are some for the 505. For crossword puzzles and sudoku, you could just download a bunch, put the files on your reader, and then use the notes function to write in solutions.
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