"You cannot discard check out because there is no checked in version of the document. Please delete this document instead. "
During job creation check the "Defer required" option.
Behind the scenes what the option does is switch the target column setting to “Optional”, then copies the content, sets the metadata, checks-in the item and finally switches it back to “Required”. The end result should be a checked-in item (document or list item) and a required column without a value. Of course, it will do all this without reporting that error. To the end user the document should accurately reflect the source metadata (empty fields), be checked in and they can continue on without that dreadful error message, if they so choose.
The next time someone goes to modify this item in SharePoint, SharePoint will require that they populate this column with a value before saving, but this is SharePoint’s behavior which should be expected.
This will only work when the target is SharePoint 2010 or Office 365; the source (SharePoint 2003/2007, File Shares, Public Folders, etc.) does not matter. The option will be available for all operations, including Site Copy, List Copy, Item Copy, CSV Uploads, etc.