Good morning, @jswhitne ...
Thank you for providing a link to the Guide that you referenced in your question. In looking through that Guide and searching for the word "eight", I'm not sure that I would agree with you that the "Help" menu can only accommodate up to eight links. In the first paragraph of the blue box at the top of the Guide you've linked, it says, "Depending on their role, users can view up to eight default help options." Further down the Guide, under the heading and supporting screen shot for "Customize Help Menu Links", it says, "You can allow your users to view up to eight default Help menu links according to their role". When I read those sentences, I interpret that to mean that Canvas has provided us "out-of-the-box" with eight default menu options ... all which are described in the bulleted list under that "Customize Help Menu Links" heading. You can include all (or none) of these, and you can also add your own custom links that you want your faculty and/or students to have easy access to. For example, we have 13 links in our "Help" menu. Some of these are the default ones that Canvas provides to us...some we've chosen not to display to anyone. Other links are custom links that point to other areas of our school's website. Some of these links are only shown to students, and others are only shown to our faculty.
I would also say that filling up your "Help" menu could be a bit overwhelming for people. If you wanted to try and condense the amount of links that you have within the "Help" menu, you might want to consider creating a brand new Canvas course shell that is set to "public" so that you don't need to enroll folks in it. Then, create a page or two within the course...maybe one for students and another for instructors. Then, place all relevant links for that role within the page in the course. Then, once you have those pages created, grab those page links and add them as custom links to your "Help" menu. That way, you not only have a couple pages that contain relevant links for specific roles, but you've also saved a bit of scrolling on the "Help" menu (because not everyone uses the same screen resolution), and you have a bit more freedom in designing a nifty looking page with the links you want to display. 🙂
If you have any other questions about this, please feel free to reply below. Hopefully this has helped to give you some ideas. Take care, stay safe, and be well.
