I am familiar with the Triangulate (but seems I didn't apply it) but what, if I may ask, does the Limit Dissolve do?
Limited Dissolve arbitrary simplifies the mesh topology by getting rid of vertices and edges on planar faces. Most of the time it creates ngons.
That is why Triangulate Faces should be applied afterwards.
The reason I suggested it, is because overly complicated mesh (with holes) does not work well with Physics SelfMesh.
It might create some sort of abnormal partitions inside the hole preventing objects from going through.