The console app would be the place to find a doubleTwist exception error if that is what is happening. Could you run Console.app (it's in Applications/Utilities) and then run doubleTwist again? Then switch back to Console.app and see if there's any doubleTwist error messages.
Here's what's happening when you sync/transfer files:
First dT must scan and analyze the files you've selected for transfer to check for format, compatibility with your device, necessary transcoding that must take place (or none), codec irregularities that our transcoder can't recognize, and anything else that might cause file to not transfer correctly.
This process must take place before transfer can begin and before anything begins to display in the progress bar. If you're transferring a large amount of media this can take a while.
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