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Maybe I'm missing something in what you're describing but I haven't had any problem at all.
Admittedly the only thing I'm bothing to put on my Reader is .rtf and .txt files. and that has been simple and fast.
I just got to the directory containing the files on my hard drive. then Drag them to the Sony Reader entry in the left column. That's it. I'm not even sure what the Import function is supposed to do so I havent bothered with it. The Reader handels rtf and txt just fine so I'm happy with it.
BTW moving a PDF to it is the same process. Drag and drop on the Sony Reader entry in the left column.
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