This is my biggest frustration with Layout and it's why I'm learning other programs. I honestly don't understand what some posters in the "How can one honestly ... " thread mean when they say dimensions are associative in Layout. As far as I can tell, dimensions do not align with their leader points in Layout, they do not align with the plane of the geometry they're associated with, and they do not update if you alter the model in SketchUp - therefore they're not associative.
I do wonder if this function (aligning dimensions with geometry in perspective view) is a difficult task for programmers because other programs also lack this feature. Rhino has full annotation capabilities but only in model space. Once you initiate their Make2D command to create a 2D vector line version of your model, the dimensions disappear. Rhino is miles ahead of SketchUp/Layout in annotations overall but SketchUp/Layout has vector and vector / raster hybrid output in perspective views - which is unique to the programs I use. If they could solve the problem described in this thread they would very quickly become my layout program of choice and I imagine others would agree.