Answer:
Yes, it would make it back up.
Step-by-step explanation:
If it has 100,000 Joules of gravitational potential energy at the top of the hill, by the time the cart gets to the bottom, it will become PE = 0, KE = 90,000 since 10% of 100,000 is 10,000. The cart only requires 80,000J to climb back up so it should easily do so.
I didn't quite understand if the 10% energy loss is total, or every time it goes up or down, but it isn't a problem because 10% of 90,000 is 9,000, which means it would have 81,000J of energy on the way back up IF it loses energy due to friction on the way back up also.
The only physical law you need to prove this is the Law of Conservation of Energy: no energy is lost, only transformed; 10% of the energy becomes heat, the rest remains mechanical energy, which is the reason why the reasoning above works.