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My client on a Terminal Server 2000 running Outlook 2003 had this error when he started Outlook

Outlook failed to start correctly last time. Starting Outlook in safe mode will help you correct or isolate a startup problem in order to successfully start the program. Some functionality may be disabled in this mode. Do You want to start Outlook in safe mode

I found the solution at http://www.technize.com/2008/03/14/outlook-failed-to-start-correctly-last-time/
Solution:

The solution to this problem is rather simple. Only deleting the following key will solve the problem:
Navigate through these items with registry editor REGEDIT and delete the Key Resiliency
HKLM
Software
Microsoft
Windows NT
Current Version
Terminal Server
Install
Software
Microsoft
Office
11.0
Outlook
Resiliency