@SandaZG
My presentation won't share much more on the topic than what I gave here. It's very high-level, which is unusual for me.
The use case you provided Chris sounds a bit more complicated than mine. I'm automatically uploading lecture notes to Canvas every time I update them on my Windows machine. I only have one course and don't have to tie it to a specific student.
Are you uploading the files to maintain an archive of them with the course, submitting the work for the student, providing feedback to the students, or something else?
Other people have requested a way to bulk upload files (for submission feedback) that were not bulk downloaded. The problem is the naming scheme. Canvas needs to know which student and assignment the submission is for. If you were doing this for multiple courses, you would also need some way to identify the course the student belonged to.
If you are just archiving the work but the students don't need to be able to view it, then it could all be handled by the folder structure in Windows and as "simple" as mirroring the folder structure to Windows. I don't know specifically where anyone has done that, but I do know that people have asked for WebDAV capability with the Canvas filesystem. The answer is that Canvas doesn't support WebDAV, but searching for that might lead you to where someone has written and shared a script.