Waypoint addition via route planning in MAP VIEW

Currently cannot plot way points off non-highlighted roads/trails in the Magellan software in Satellite or Map view.  Have to use Satellite because the roads/trails I want to map do NOT appear in Map view. 

Need to be able to plot waypoints on both satellite and map views.  

What I have found interesting is that while we are out on the trails and using the TRX the map/trails appear on the unit but do not appear on the Web base route planner.  This should be corrected.  

Off to use another map source to plot our courses.  Shouldn't have to but, what needs to be done to get this system to work.