Just thought I'd share a couple things that made this achievement easier for me, because the controls on the WP make this one of the more difficult achievements. I had been using the gas pedal/steering wheel combo up until New York, but the counter steering kept messing me up, so I switched to the arrow keys and found it a bit easier maneuvering the truck around.
The biggest tip that I didn't realize until I was about halfway done is that you only need to park the front piece of your truck in the zone. The trailer can be absolutely anywhere and it still counts. I had been agonizing over lining the whole truck up but just make sure you have the front part in the lines and eventually you'll be 3 starring all the levels in no time.
Level 8 and 9 were the hardest ones, so once you're past them the levels will get a bit easier.