Is this now possible if Insync is used on both Windows and Linux using the same shared folder with Insync File Matching. (Unlike the Original Poster here, who wanted to use Google Drive on Windows and Insync on Ubuntu).
File Matching - File Matching is here! (New Insync version: 1.3.0) “Insync will now try to match your local (in your filesystem) and remote (in Google Drive) files to avoid duplicates and unnecessary uploads and downloads.”