How do I force a "Waiting" file to upload to iCloud?
I was concerned I'd have to save these documents to my local filesystem, delete them from iCloud, and then perhaps save them to iCloud over again, but it turned out that simply re-opening the "Waiting" documents, making a trivial change to them (such as deleting a character and then adding it in again), and then saving the file caused them to be synced successfully.