Sorry I can't get the updated video up in time with me popping the challenge, I have been just too busy with the end of this semester. I recorded it yesterday but have had no opportunity to edit it or upload it. The video at the bottom will have to suffice, but I hope to have proper ones in the coming weeks as I will be done with finals soon.
A similar challenge has been offered twice in the last 7 months (once in late June and once in late August) if you remember either or both
then this will just be a refresher.
For reference, getting a 'Triple Pass' skill is pretty much while racing pass 3 cars in quick succession. Even with load and reload times this shouldn't take more than 5 minutes to do, since you only need 3 'Triple Pass' skills.
Any race should work, just change the Drivatar difficulty to 'New Racer' to improve your odds. I personally just used the Coober Pedy Scramble race (and is shown in the video) and well over half the time I get a 'Triple Pass' skill almost by accident. The race just north of the Coober Pedy Scramble, Cross Track Scramble, also works quite well. Do an exhibition race, blueprint the race to 'Anything Goes', 1 lap, and pick a Classic Rally car. It will probably make this easier to fully upgrade it. Let the other racers get a little bit ahead of you and pass them when they are 'clumped' together. It is faster to restart the race rather than rewinding or letting the pack get ahead of you again, as the vehicles are more 'clumped' together at the start of the race.
Load times edited for brevity. Ignore the first challenge popped, that isn't applicable to this set of challenges.