It's a great system. And easier than you'd think. It really takes only two days of logging-in to learn a random password; even a long one. After all, how often do you think about your password when you type it in? I imagine you only consciously think about it the first dozen times you type it, and after that it becomes muscle memory, regardless of whether it's a random password or a memorable one. If that's the case, why not just use a random password to start with?
Still, it's never good to encrypt everything with the same password otherwise you end up in the same mess as the OP. What's the point of a backup if it shares a common point of failure?
Still, it's never good to encrypt everything with the same password otherwise you end up in the same mess as the OP. What's the point of a backup if it shares a common point of failure?