How about this: If there's any chance you'll need extended downtime for maintenance, announce it ahead of time.
I'd much rather you tell me servers will be down until 3, and bring them up early if able, than to tell me they'll be up at 11 and then have to extend it.
Its a trust issue.
Us being able to trust your announcements, and us being able to trust you to know your job well enough to anticipate that a given hotfix will take up to 25% longer than a normal maintenance period. Because, believe it or not, some folks have a lot to do in a day, and scheduling around your maintenance is a necessary (and admittedly nerdy) evil.
Thanks,
Lancel
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