How can I make OSX to upload files to icloud?
The menubar app Bailiff lets your pin files on your drive and evict them without needing to wait for the background processes to do the work for you. 


https://eclecticlight.co/cirrus-bailiff/


Once you’ve got the files removed, you still need to wait for snapshots to purge. The df command isn’t going to show you purgeable content, so this tool. It might not be sufficient to fix what you’re trying to do in the end, but it does do what you asked.