A command line utility to test the status of files in iCloud drive directory
Solution 1:
You can use brctl status.
It outputs alot, but you can grep pretty easily, for example brctl status |grep needs-sync-up |cut -d'"' -f2 will show you all files waiting for being uploaded (without their path), or use brctl status |grep 'somefile.ext' for checking the status of somefile.ext.
See brctl --help for more.