GMAT Critical Reasoning (CR) | Re: John usually sorts incoming mail, such as bills and legal papers, into

If history is not to be taken into account then why are we focusing on "pre-sorted" mails in option "E". That's clearly out of scope of his hypothesis then.
Because "pre-sorted" is the outcome of the first scenario (if used in the future). When you compare two scenarios, one of which John have to select, you can't compare them taking history into account. It is just incorrect approach to analyzing pros and cons of different scenarios (in GMAT)