One of the advantages to having a friend who works at Microsoft is that requests to have Bill Gates’s tires slashed if an alleged feature isn’t reworked can be easily forwarded. Not that this has ever been done.
But presuming Mr. Gates is reading my Away Message:

Outlook, while allowing multiple signatures to be stored, only allows 1 (set as default) to be displayed on outgoing e-mail. If a user wanted a different one, they were instructed by the help file to copy and paste the stored signatures buried in submenus. Besides being ridiculously inefficient and dumb, this is no more a feature than being able to manually type in signatures character by character for each e-mail would be.