I was thinking that with the increasing popularity of 3d printers that might be the way to go. Have it print out the hill with slopes from one contour line to the next then glue the photocopied map onto it.
I can see some issues with this. If using plexiglass they will have to sit on top of the glass. They are going to be easy to shift around by mistake. I'm thinking of maybe trying to get them to stick with some sort of putty.