Hello @rafe_sholer ...
If you would like to see an indicator for file sizes displayed for students when they submit work, I would recommend that you submit it as a Feature Idea here in the Community. That way, other Community members can also evaluate it to see if it would be something they would also be interested in having as a part of the core Canvas product. Here are a few Guides on how the Feature Idea process works:
For example, you could create a Feature Idea and reference this Guide: How do I submit a media file as an assignment subm... - Instructure Community (canvaslms.com) ... noting that it mentions a file limit here, but not within the Canvas interface.
As I was typing this reply, I just thought of something else. It's my understanding that media files are uploaded to a separate media server compared to other file submissions. I tested this in my own sandbox course using a dummy student role. With that role, I uploaded a MP4 video (a 5-second video clip that was under 1.5 MB in file size) to a Canvas assignment using the "Media" tab to submit the video (similar to the instructions in the above link). When I checked the dummy student's personal "Files" area to see if that MP4 file was in the "Submissions" folder for the course, I did not find it. So, that confirms with me that the MP4 file is not uploaded to the personal "Files" and is instead uploaded to a media server. It is still true that that there is a 5 GB file limit for regular file submissions, but I can see how it would be helpful to know within Canvas there is a 500 MB limit for media submissions. I think the thing to keep in mind is that media submissions are separate from regular file submissions...even though there is no visible indicator right now of those limits in Canvas. That's where a Feature Idea submission might be helpful.
I hope this helps to clear things up. My apologies if I didn't quite understand your question earlier. Take care...