I'm pretty sure I'm doing something wrong, maybe when creating the UV maps and was hoping to get some help.
As you can see here:
The wood on the front of the house seems ok, but for the wood at the left side it seems like painter doesn't apply the pattern for OR shows the front facing faces of the wood mesh, but it does show the back side of the faces.
I've attached a photo from blender just to get a sense of how it should look: 
Update: Seems like mirroring the meshes for the faulty wood bars did the job, but why? Doesn't a mesh keep its properties after being rotated/mirrored?