Can you encrypt not just the private key, but also the public keys (ie bitcoin addresses) in an Armory wallet? I would imagine that the paranoid darknety bitcoin user has an interest in keeping not only their private keys safe (so nobody can steal their bitcoins), but also has an interest in keeping their public keys safe (so nobody knows what addresses they control). With bitcoin armory, at least by default, a wallet's public information is available without any password protection when you load the program. Is there an option to encrypt all the wallet's information, so you can be safe in case, say, some jerk steals your computer and scrapes it for information about you?
I would get a Tails USB and store the Armory application and wallet files in encrypted storage. That way not only can they not tie your addresses to you, but if you access bitcoin related sites only through Tails, it would be hard to show you even know anything about bitcoin.