Even with the best maintained OHLE, misalignment of the conductor wire through lateral movement or insufficient tension is the most likely cause of dewirement. Headspans can introduce movement of adjacent conductor wires when a train passes at high speed that would be less likely on wires where each conductor and catenary wire is supported by individual registration and cantilever arms respectively.
The issue with headspans is that if there is a single case of a pantograph getting above the contact wire at any sort of speed, there is a high chance of all wiring supported by the headspan being out of service. Not necessarily that much of a problem on twin track where the possession to fix it would probably close the other line anyway, however, when it involves a four track stretch, then it usually means that a major route is completely blocked. So in terms of delays per incident, the impact can be much worse than with individual masts or gantry span wiring.