I've just rolled out MS Outlook 2003 to 55 pcs with virtually no swearing or tantrums. I decided to investigate the automatic software deployment options that come with active directory and MS Windows Server 2000.
It took me about an hour to setup the silent and pre-configured installation script and then a few test machines to test the rollout. Made it all active last night and by 10am this morning all but a handful had the package already installed - cool!
Had a few teething problems that I'm sure I can sort out but it's definately the way to go.