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I've had the same problem with my kindle fire not connecting and tried much of the steps you listed as well and nothing worked. I'm thinking about getting a can of compressed air to clean out the usb port in case some debris is in there but otherwise I'll just wait. Another idea I had is to update the firmware to see if that will also help with connectivity issues. As far as getting your files on you paperwhite I'm assuming you got most of those files are from the internet. You might try to use the experimental browser to download some of those files directly to your paperwhite.
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