Its plain and simple

[DoT]

Well, that just makes the skybox cast light on nearby objects, I believe. So they are most likely not in the line of sight of the sides of the skybox, and too far from the top.

I ended up just evenly adding light entities in the sky of my map, to aide the light_enviroment. Ended up looking very normal to me.

You mean like over the skybox add some light entities?
I'm uploading a vid that I made of the map to youtube so you guys can see what I have now.