Sean,
Outlook rules are limited in this fashion. if a Distribution list containing x amount of user address will not be properly filtered because the DL is Y address. Rule filtering will only see the public group y address and move any emails from that group to a specific folder.
Since you have reached your rule limit then creating a rule for each individual contact is going to be difficult to resolve. You could maybe create a customer rule to move the email based on the individuals specific address.
This is something i have not tested myself but worth a shot.
http://office.microsoft.com/en-us/ou...010223243.aspx