Generally i think the practice by people in the long run will have to involve a checking and a savings wallet, where best practice should be leaving no more than 500$ worth in the checking wallet.
That way, a wallet with more usability can be held, for mobile devices, "simple" password security and such. On the other side, due to the nature of bitcoin, a secure savings wallet should be promoted, using physically external security features such as a mobile auth app or a smartcard.
Once the development for such a second tier of defense is there, usage of such should be heavily promoted by bitcoin.org, after all users need to be protected from their own stupidity.