Also, why are there weird one-sided squares showing up anywhere I change the edges of a brush using displacements?
How do I fix them?
(I can't fix one thing without breaking another, lol...)
A displacement is "hosted" by the face of a brush. So on a cube brush, you could (if you really wanted) have six displacements, one replacing each side of the cube.
Generally, people put down a rectangular brush and turn just the topmost face into a displacement. The other faces are left along and textured in nodraw, and are harmlessly left below the surface.
Depending on your settings, Hammer may display these faces to you. Check the D* buttons on the top of your window (ex. "DW") and look at the tooltips for those and see if toggling them changes what you see.