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For video you need to reencode from high profile to whatever is not high profile. (Sorry, I'm on painkillers after an extensive root canal.) There's a thread at XDA giving a correct handbrake profile to reencode your video. IIRC, it's an issue with the OS.
For Calibre what I do is start up the Calibre content server and then use the browser to access it and download from there. Your books must already be converted or in the correct format.
If I wasn't very clear, it's the pain killers.
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