This question also brings up the issue of map projections. The shortest course may not be a straight line on your map, but I'm not sure if the sim accurately represents this. When plotting a course to New York, for example, it might be interesting to first set a straight course (on the map) with one waypoint half-way between. Then drag the middle waypoint north and watch the distance to the end waypoint. The total distance should decrease until you find a minimum value. Doing this with multiple waypoints should allow you to find a 'great circle' course between points (again, if the sim accurately does this).
I will have to try this tonight, and I will report back.
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