Hi Matt,
Since Aspire assumes that you are going to mill a 3D object out of a block of wood referenced from a flat plane, I am not sure how you would accomplish what you want to do with a single tool path. Caveat here: there may be a way, I just do not know how to do it. That is the bad news. The good news is that it is fairly easy to do. Break your tool paths into three sections. The logical choice is the left block with curve, the center ramp and the left up ramp. Create two rail sweeps for all three. Select the left section and create tp's for it. Now select the center section and when creating the tp reset you start cut depth to reflect the height difference from the top of the left to to top of the center. Do the same for the last piece. If you are using the same area clearance tool and the same finishing tool you can save out all three area clearance paths to one file and the finishing tp's to another. Run the first swap tools and run the second. The would be a fair amount of air cutting on the last part but this would speed it up tremendously.
Dan