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I have had the strange characters too...the titles/author names were typed in using regular letters, and were fine in the "Library" but showed up after the transfer to the reader.
As for the metadata, I have found that if I uploaded a txt file, for example, and changed the metadata in the library, converted to epub and then transferred, it would transfer the txt file with the original metadata to the reader. I've had to "send specific format" or delete the txt file from the library.
As far as limits, I've been pretty lucky with transferring 20 or so at a time. However, last night I put about 100 on my SD card and this morning they aren't showing up. So, I'm not sure about the limits. Maybe someone else has more data.
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