A colleague of mine at Microsoft, Jeff Jones, has written a thought provoking couple of articles on security patches/bulletins/errata and 'customer pain'. He does this primarily to help improve the security update experience for Microsoft customers, by analyzing issues and providing guidance on remedies to make the life a little easier for folks.
Have an open mind when you read these!
Security in Operation (Part 1 of 4): Windows, Linux and Security Notificationshttp://www.microsoft.com/technet/community/columns/secmgmt/sm0305.mspx
Security in Operation (Part 2 of 4): When an Issue Affects Multiple Productshttp://www.microsoft.com/technet/community/columns/secmgmt/sm0405_2.mspx