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Could anybody tell me why I'm getting this weird issue when I punch a hole through a plane with a boolean? I know it's something to do with tris but it causes issue when applying a material over the top. It's like the normals are the wrong way round but only from certain vertices.

enter image description here

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3D software needs to interpret faces with 3 or 4 vertices. Everything else is called n-gon. In this case you have an n-gon with around 26 vertices. Select this face, hit x, delete just this face. than select two vertices in corners (drawing), press F to create edges between them, than fill everything out. With 3 faces this should be solved. You can also try to press K (knife tool) to draw the missing edges. enter image description here

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