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I updated around 6500 machines on our core network to 8.5 from 8 mostly in the middle of the day when they had outlook 2003 open, I had about 40 calls for this in total (across the entire rollout period), and as I had already advised the service desk how to resolve this in 5 seconds flat this wasnt an issue.
You could get everyone to leave their machines on over night (with outlook closed) and do your rollouts then, but to be honest it wasnt that much of a big issue for me.
Yep, We did ours after hours and asked all users to leave the computers turned on over night..
Hope this helps.
Thanks for providing me with your own experiences. It looks like I need to make sure the help desk is notified of the change so they can quickly help those that have problems. Then I'll push out the upgrade at night over the course of a few days.