Hi Lea -
When observing multiple children, the dashboard and calendar can get crowded. You're right!
On the dashboard, you can nickname and/or color code the course cards. Those choices then follow to other places in Canvas, like the Calendar. That will make it easy to toggle on/off the courses you need to see on the Calendar at one time. (ie: my mom could click all of the K [course] items to see what I have going on, but turn off all of the ones with my sibling's initial) I go through more detail about this in Clarity for Canvas Observers, too. If you have any questions, I'd be happy to collaborate! 
There's a feature idea https://community.canvaslms.com/ideas/8649-parents-toggle-view-between-children?sr=search&searchId=6... that you may be interested in. Feel free to vote and add comments to the discussion. Feedback from observers is always valuable.
I think the easiest answer for you is to use Canvas Parent. If you'd like to get an at-a-glance view of each child's school week, the app looks at one child at a time with a weekly planner view. It's great for understanding what is going on at school and how you can coach them through the week. It doesn't have as many functions as the browser, but I think it's easier to navigate to the key information. (Observer Role vs Canvas Parent)
Good luck!
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