The .exe launcher that javapackager uses on Windows is a "Windows" application and not an "Console" application. As such, any output to the console is lost.
This is the equivalent of running the application with javaw.exe instead of java.exe
Perhaps the application could remain a "Windows" application, but attach to the console of the parent process if possible.
https://msdn.microsoft.com/en-us/library/windows/desktop/ms681952(v=vs.85).aspx
http://stackoverflow.com/questions/574911/difference-between-windows-and-console-application
This is the equivalent of running the application with javaw.exe instead of java.exe
Perhaps the application could remain a "Windows" application, but attach to the console of the parent process if possible.
https://msdn.microsoft.com/en-us/library/windows/desktop/ms681952(v=vs.85).aspx
http://stackoverflow.com/questions/574911/difference-between-windows-and-console-application