I would love to see an option where we could tick a box and on importing an old class file from another LMS (D2L for us) Canvas would ignore anything that isn't on the root level when crawling the file. At the moment it will just fail out with a generic "contact support" message and you have to remove any further directories. Not a huge deal, just not how I was expecting it to work.
This would be exceptionally easy to implement, but it also isn't something that comes up much if at all. I am not aware of a situation where it will handle other directories, but there could be one, this is why I propose to add the feature as an option.
If I am mistaken in how importing works in Canvas, I would love to know more; I went through the admin guide yesterday quickly and I couldn't find anything in the 10 minutes I took. I just found through trial and error that it wouldn't take the file if everything wasn't in the root.