Hello,

You can accomplish this type of functionality by creating an Alias and adding each of the accounts to the alias. This will allow you to both send (optional) and receive email to those addresses. 

Is there then any way to push out that contact list to Outlook? I know if I went to WEBMAIL and CONTACTS it would be listed there under the global address list... But then I would have to EXPORT that to Outlook and in the past that would cause issues every time I did an upgrade to SmarterMail it would break it.