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Hmm, I'm using it in Windows XP on a bootcamp partition on my Mac. I have done it both by running the app straight from the card in a cardreader as well as from the DR1000. Both in the WritePads folder and in my own folders.
It only works with PDFs as far as I can tell, but even when I tried with a PNG image, it saw there was scribble and made the Merge icon active (even though it didn't do anything)
You have certainly gone out of the way trying various things for something that should be straight forward. I'm stumped. The only thing I can think of is that perhaps the matadata.db is corrupted and not read correctly. Did you try deleting it and start over with a fresh scribble (maybe restarting the reader to be extra careful)?
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