I have tried several times to insert multiple via-points in routes with the hand tool (not using alt key), but after a several are added the next insert will take place before the last inserted, instead of between the 2 via-points I was working with. And the only way to get around it is to undo the last point, switch to the insert pencil tool and continue. Also calculation will take a very long time then.
Create a route with only a start and end waypoints or via-points, let say 100km on a City Navigator map (I tried both North America and Europe NT(U) maps). The begin from the begin to add via-points by dragging them with the hand tool to a road next to it. Keep continue a few times, But look carefully, at the moment the route begins to show loops, stop and try to move the last inserted via-point with the hand or move via-point tool. You will notice if you look to the rubber bands that the via-point is inserted in the wrong sequence.
Say I have A and Z as via-points for start and end of route, till F it goes (assume) well, the point inserted after F is G, but its inserted before F in the via-point list and not after.
This is what should happen: A B C D E F G ........ Z
This is what actually happens: A B C D E G F .......... Z
BC 4.3.5 Windows.