I really liked your project; it's one of my favorite types of hardware that I've seen modelled in Technic.
I got to thinking that you might be able to make this project work by 'adding energy' to the passenger car at the bottom of the hill. When I was a child, I had a toy that had this wheel at the bottom of the hill that spun very quickly. The passenger car would contact the wheel and would accelerate to sufficient speed to climb a hill and perform a loop, then coast down a hill back to the spinning wheel. I'm not sure if this is feasible for your model, but I thought I would mention it in case you still have the model and wanted to try it or something similar.
Thank you for sharing your work.