I just heard that someone lost 150 coins in an offline wallet with a 20 character strong password and he doesn't understand at all what went wrong
It so obvious to you when you get to gloat over other people's losses, but I've yet to see you speak up in a thread where people are advancing "brainwallets" and say "no! don't do it!". 
I don't trust my memory very well. And I know that some one is using a dictionary attacking method to search for all possible brainwallets
BTW, I did not laugh at his loss, but at the fact of lacking of easy way to secure the wallet for normal user. And there is another potential risk of losing bitcoins when a wallet has made more than 100 payment thus the old backup does not contain the newly generated address
Anyway, current solutions are either cumbersome or risky. Armory is the right direction, but in order to use it you have to understand the technical details of each transaction, not for average Joe either
Just came over this poll:
https://bitcointalk.org/index.php?topic=313029.0