I have created a python script to place a multiple of leaders, using AddLeader(points, text=name). depending on the Dimension settings, these appear with seemingly random oriented text, some are mirrored horizontally, some are ok.
Rotating the viewport to view these from behind flips the situation good>bad and bad>good.
Setting Text alignment = above dimension line or In dimension line : 
Setting Text alignment = Horizontal to view:
Placing leaders manually does not cause any problems.
Max.
From the Help:
view_or_plane
Optional. String or Plane. The title of the view.
If a view title is specified, points will be constrained to the view’s construction plane.
If a view title is not specified, points will be constrained to a plane fit through the list of points..
Fitting a plane through your points will result in random normals, so this will likely never be reliable… I guess I would try and concoct a plane to be passed with each leader to be sure of my orientation.
–Mitch
Mitch,
I duly noted that method in the example you showed in my other thread, but I figured this to be easier to script, in the assumption that Rhino would manipulate dimension text to be readable (like it does when placing leaders manually).
Well…, in hindsight at least. Anyway, I am happy with the “Horizontal to View” setting, but I thought I should mention it.
Max.
Well, scripting methods “assume” less then their Rhino command equivalents, they’re more basic… That means the scriptwriter generally has to code in the additional functionality themselves…
–Mitch