We need to just get away from remembering passwords. Something like Mozilla Persona would have been great, but since it didn't catch on we already have KeePass

We need to just get away from remembering passwords. Something like Mozilla Persona would have been great, but since it didn't catch on we already have KeePass (and for mac/linux, keepassx2 alpha works quite well). These cutesy little passwords might be fairly strong and easy to remember, but it hardly matters because having to remember them results in reuse and an upper bound on the possible entropy. The human mind has more important things to do than remembering thousands of bits of entropy (spread among all your passwords, you should have at least that much)... we made computers to remember this sort of stuff for us. If these passwords aren't meant to be remembered, but put in keepass, then there's no point in not just upping the entropy by randomizing at the character granularity. KeePass makes it much easier; you have it generate you 300 bits of entropy passwords (or whatever you feel is enough), and then you can focus all your security efforts on that one database file. Having a "single point of failure/password" doesn't have to be bad because it lets you guard more closely against that single point.