I have found that placing dimension can be effect by the point of view the dimension is placed.
But that's in the 3D environment. Once you have a 2D view, it can be imposible to get what you want. To work around that, I do the following.
I create a named view in 3D showing what is desired including the dimension. Then show that named view in the 2D draft. The problem is you are no longer using the drafting scales to control font size. The Scale/text game has started and can be a pain to set up right.