Here is a visual of how Tristan plans her year by day. I do something similar with a calendar and pencil.
When we both are comfortable with how it balances out, then we take the time to enter everything we have selected for everyone in the O. Once it is in there, we don't have to stress (think) about it too much anymore, because we've already figured out the schedule.
Everyday I print my check-off lists for all of us, and enter what we worked on/finished in the evening. If I miss something one day, it is okay. The O automatically reschedules that assignment for the next time we are doing that subject, whether it is tomorrow or next week.
Because I spent a lot of time in the beginning adding our resources for the year, I give myself that time later to be with the kids and enjoying our school instead of always having to stress about my paper planning, getting behind, and all that goes with that. Ack! I'm stressing just remembering that situation! ;)
My kids love their lists and all of their stuff is in the O - from geting up and doing their morning routines (easy checkmark and gets them into the accomplishing of it all), to what they're doing in school, to their church program activities, to their chores. This allows them to learn how to plan their day, what has to get done, and what their limits for extra activities are (no swimming if your school list isn't done) and allows them to work independent of me (to a certain degree). That is worth the cost of the O to me just for that. lol