Scott,
I have a feeling that I did not understood your point, sorry :-)
If the recipient is either the mailbox or the contact in the AD, administrators could set the limits for that recipient. If the recipient is beyond non-authoritative contact, the SMTP connector could set the limitations. And if the case is pure relay, then that hits to your global limits.
And about CEO scenario, E-shell does not make this easier. Quite often you do have some others who needs higher limits, so you have to think about updating users activate and deactivate higher limits. This has been done by people who are family with GUI. Think about how many human mistakes this might cause?
So basically, could you tell why I have to modify every single mailbox in Exchange organization to make one small group to work? Instead of modifying this tiny group and rest of people are working automatically since the first step?