I don´t think there is a trick, at least I didn´t find any work-aroundt-the-feature.
I guess the tracks are hordcoded on the map as splines (if you look closely you see some tracks/rails are making funny little loops). If the spline of the waypoints doesn´t fit the hardcoded spline by good margin, the waypoint spline breaks up. You basically have to set a lot of waypoints (especially around bridges, some bridges refuse to be passed by a train at all) and take care that the white line in the FMB doesn´t interrupt and the order of the waypoint numbers is always ascending. If there is jump in the waypoint numbers, you see there is something wrong and the train will stop at the jump or interruption.
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