afaik itunes can't auto update like that. but i don't think PadSync will do that either, unless you alter the copy in the Library directory and it will detect an modified timestamp and update the copy on the iPad.
I can probably test this out if you want me to, or you could try it with the demo copy..
another use for it, keeping 2 devices in sync with the mac. since it auto syncs the files you could have it pull down changes from one device and push the updated file to the other device. itunes can't do that without any manual work.
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