Hello again,
Just wanted to give a quick update, I was able to create the 2D Map of penetrations.
I started by converting my DEM to a raster. I then took the 3D dwg of the airspace, converted those individual pieces of the airspace to a TIN using the z-values as the output (I needed to preserve the negative outputs and decimals), and then converted those TIN files to rasters.
I then took those rasters, and Mosiac'd them at 32-bit to keep the negative outputs and decimals. After that I then took the raster of the DEM and the Mosiac I created, and ran the Minus function to extract only the values where the terrain raster penetrated the airspace.
I took that output, converted that raster to a polygon, then symbolized it on top of the rasters I mosaic'd. For now, the client did not want a gradient of exact values, they wanted an overall picture of where the penetrations were, so I dissolved the layer to create on full polygon.
Below is one of the outputs I created, the client was very satisfied with the visual.