Hi Matthew -
It definitely is more complicated to observe more than one child through the browser. You can color code, nickname, and drag-and-drop to reorder courses, but there's not a way to look at one student's information at a time. (Clarity for Canvas Observers)
Have you tried using the Canvas Parent app? It's really great for seeing one student at a time. While it doesn't have all of the features as the web, it's a wonderful starting point for conversations. (Observer Role vs Canvas Parent)
If you have a few minutes, it would be great if you could vote and comment on this idea: https://community.canvaslms.com/ideas/8649-parents-toggle-view-between-children" modifiedtitle="true.... I think it would be helpful to you and your family, and it's always valuable to hear from Observers.
If you have any follow-up questions, please reply! 
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