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How about a new way of looking at the problem. It's not perfect, but neither are any of the above options, and this one is super easy to implement.
I have a laptop with a card reader inserted into the expansion slot. This reader just lives in the laptop, as if it were built in.
Instead of managing two working copies of the folders (one on the PC, one on the reader), use the card for all of your work.
When working on the PC, put the card in the PC's card reader, when working on the reader, insert it into the reader. Now you are always working from the same PDF file, and it is actually easier to move the card around than to deal with connection cables, etc when attaching the iLiad.
As far as backup goes, any backup utility should be able to simply back up the card when inserted into your PC.
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