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This may not help, but I thought I'd throw this out there. I had a somewhat similar situation with my 600, where it would hang up during sync. I found a solution somewhere on this forum (I don't remember where, so I can't credit the angel who solved my problem) that fixed my problem. Maybe it'll work for you. Here's what I did.
I opened my Sony Reader Library software without my eReader connected. In the left-side panel, I clicked "Books" under "Library" so that the books I've imported showed in the right-side panel. This next part might take a while if you have a lot of books -- I double clicked each book I have to preview them (or right-clicked and clicked preview), until I came to a book the software couldn't find. I deleted that book, re-connected my eReader, and everything synced up just fine. Afterward, I re-added the book I deleted and synced again. I haven't had a problem since.
I have a friend who recently got a 300 (I think) who had the same issue. The fix worked for her, too.
Good luck!
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