Originally Posted By: Eugene
Logistics is the big hurdle there, each time you want to make an update you'll need to fetch the mail, decrypt, save, edit, re-encrypt, resend, delete the old, etc. Plus keeping track of more than 10 or so documents.


Just put the docs (with or without individual encryption or steganography) in a single TrueCrypt container file using a strong encryption algorithm and a strong password. Do some Googling for tutorials on how to compose a truly randomized password (hint: one of the simplest methods uses Vegas-grade dice!).

Then put this 1 file into "the cloud" online, with the original on one (or more) of your home systems. Use Google Docs, Carbonite, whatever (maybe more than one). When you revise the home system master file, delete the old file from the cloud and put a copy of the new revision back up there. No need to decrypt & edit docs within the clouded file, just overwrite it with the latest version. Consider keeping a copy of this master file in your safe deposit box and/or with a friend/family member. Updates to these other physical locations are more tedious but they provide a backstop against losing everything. These updates can be done less frequently than the cloud, at the risk of losing a bit more data.

TrueCrypt really simplifies a lot of this work. The key feature of TrueCrypt is not the encryption; there are plenty of good encryption tools out there. The key feature of TrueCrypt is that it allows you to put an entire directory structure into a single, secure, highly portable file. There are commercial versions of this kind of software, DriveCrypt being one of them.

Keep in mind the context of the effort here. Most of the target docs we're talking about are things that rarely change once archived. We're not talking about data files that get edited every day (though there are simple strategies for covering those bases too). How often are you going to need to update the scans of your college diploma, immunization records, and tax return from 2007?