i store all my passwords / keys using a password program like keepass what is however encrypted, too, with a more simple password but still hard to guess 
So I'm guessing you can't remember all of them. Do you store them somewhere in an encrypted file ? You see at that point there's really no difference to a "wallet.dat" anymore 
keep in mind popular password savers are going to be a target for hackers as they know the mother load of passwords is going to reside there. one trojan keylogger and your done.... its best to always have a secondary device to give authorization. its much harder to comprise your phone + your desktop.
KeyPass stores passwords in encrypted files not Servers so that isn't really an issue. It does prove my point though that many people still have files where they "key" is stored for brainwallets, just like they would with "wallet.dat" wallets.