This can be done through the use of the Live Monitor.  On the right hand side of the main window, there are several buttons.  The grey button - second from the bottom - is the "Live Monitor" button.  If you click this, it will open up the Live Monitor window.  Make sure you have the correct layer selected (1, 2 or 3), and then play your video.  The Live Monitor continuously displays the duration, time remaining, and the timeline.  You can "dock" this window with the main window by clicking and dragging it in across the main window and dropping it in any of the four corners of the main window so that it is constantly displayed along with the Dashboard.

If you have an older version of ScreenMonkey, you may need to update your software.  Oliver added this in one of the later version (possibly 3.0), but it wasn't available in the earlier versions.  However, I have to say, this has been one of the BEST additions to the product.  It was helped tremendously, especially when you need to know when a video is about to end.