We can't find a way in the admin panel to enable such as feature. For instance, every Friday at 9pm, we are always raiding the same target. Can we tell the system to automatically populate this day/time every week, a month in advance? This way no intervention is needed to add it to the calendar and yet it wouldn't show us raiding XXXX mob in 2012

Absolutely.

Admin > Schedule > Event Schedule.

Then click "Add new Recurring Event" at the top.

It's not recommended that you schedule TOO far in advance (try to limit it to 3 months in advance, you can always change it later).