Heading back to my favorite spot to get this challenge done. Head to fields to the right/east of the Yarra Valley Horizon Festival. I designate my spot at the beginning of the video. Another good spot is the hills around the Outback Horizon Festival, this is just one possible solution to this challenge.
Any car should work as the challenge doesn't designate a specific car. I personally used my my tried-and-true Nissan Skyline GT-R V-Spec II again, upgraded to S2.
For reference multiple jumps in quick succession are how to get a 'Kangaroo' skill. Just get 10 of them per the challenge description and it will pop.
As shown this only takes around 2-3 minutes to do. Only thing I edited out was my crashes and flips. You don't necessarily have to bank the skill chain for the 'Kangaroo' skill to count as I was mid-way through my skill chain when it popped.