I finally discovered the cause to a problem I was having in Outlook 2003. 

Problem: Everytime Outlook is closed the popup stating Outlook has encountered a problem displayed with the check box to restart Outlook.  The only way I could keep outlook from generating the error was to pin the process to one of the cores on the CPU by opening task manager, right clicking on the outlook.exe process and select set affinity to pick one of the cpu settings.

Cause: I had kept logging turned on in Outlook.  For some reason I have still yet to understand, the log files stored in the default path "C:\Documents and Settings\%username%\Local Settings\Temp\OPMLog.log".  After turning off the logging option and deleting the files Outlook gave no further problem when closing it.
 
NOTE: To access Outlook 2003 option to turn on or off Logging:  Tools>Options>(tab)Other>(button)Advanced Options and check or uncheck the Enable Logging (troubleshooting) option.