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For #2 I keep the truecrypt file size more like 500MB. Fortunately my projects don't have big files. For old tax returns and the like I have archived truecrypt files that no longer change.

#1 is indeed a PITA. I don't know of a better alternative I trust though. In practice the files I'm changing daily are small and aren't top secret, so I zip them and put the zip file in the DropBox. Then I don't have to unmount the truecrypt volume so often.



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