Remember Password Checkbox in Windows XP - not IE


You don't. That is the prupose of the password, to make you enter it.

Would it make sense to have a password established, then give an option to automatically bypass it ?
 
As JDFan stated, you can also remove your password. You would just need to hit ENTER when the password box shows up. TweakUI can bypass this automatically since it will know which account to auto login as.

Personally, I don't recommend either option as it's a security risk. Why have a password if you are going to bypass it?Perhaps if it were a standard user account, but an admin account should definately have a password and no auto login.