"When using a controller, I can place the track on the 3 spots on the left image just fine. (Though it does have a tendency to prefer the middle spot if I don't move my stick far enough top-left/down-right) But when I have a situation like the right one, I am unable to place tracks diagonally to the right. It either goes up, or down.
This also applies to going diagonally left/up or down when it is also able to move to the spots next to it. Though I have noticed that it's a little bit easier to go up/down compared to left/right."