Started my 2nd attempt, and things are going well so far.
For the finishing pass I am going to use a tapered ball nose bit that @fenrus suggested.
I reduced the detail in the 3D model (it no longer has the city platforms or roads). I am adding that detail back via (non 3D) toolpaths after the finsihing pass is done.
I’m not sure when @robgrz added this feature, but being able to see the X,Y and especially the Z height in a 3D model REALLY made this possible. If you have not noticed that information down in the corner…
I am also going to stain the board between these two steps so that detail pops out more. Like what I did with the last topographic map.