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Did you repair/refuel the truck before you started moving it? These are the 2 best routes, I find the red one is easier if you havent repaired/refueled the white western star.
https://imgur.com/a/zRarsz3
Edit for clarification:
You can restart contracts from the contract menu where ever you are. To restart tasks, you have to drive to the place where you accepted the task (in the case of the WWS, the yellow square right next to where you found it)
I'm no expert so i'm genuinely asking. I'm only like 40 hours in this game and having fun, but found myself getting in situations where I was much better off starting over since I made a terrible choice.
It's always best to refuel / repair a truck before doing jobs like this, and let it do some of the work instead of brute force to get it up a hill.
Plus I never take the road back up (in 15 playthroughs), always go up by the powerline because it's straighter and flatter. Did it with my Fleetstar the first time.