Since SkyDrive no longer has a restricted list of filetypes allowed for upload. How hard would it be to only upload encrypted files?
A neat solution would be a client side utility that encrypts local files (or entire folders/tarballs) with gpg, generates checksums, splits them into 2048KB or 1024KB chunks and uploads those to SkyDrive. The downside is that there would have to be some sort of management/database locally (and on every machine you wanted to download the files to) that would keep track of which chunks make up which file and rebuilds everything when you download them.
A neat solution would be a client side utility that encrypts local files (or entire folders/tarballs) with gpg, generates checksums, splits them into 2048KB or 1024KB chunks and uploads those to SkyDrive. The downside is that there would have to be some sort of management/database locally (and on every machine you wanted to download the files to) that would keep track of which chunks make up which file and rebuilds everything when you download them.