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There are three types of trucking challenges. To complete the mission you will make eight deliveries.
Unlike some of the other vehicle missions, you don't immediately go to the next level after a delivery. You need to go back to RS Haul to start again. You are free to save or get a haircut or do whatever in between.
The deliveries occur in this order:
After Level 8 the deliveries vary.
There's a safe house in Dillimore that's pretty close to the mission starting point.
For the speed and safety deliveries there's not much need for tips. The time for speed deliveries is more than adequate. Use the map to plot out your course ahead of time.
Remember that trucks with long trailers make very wide turns! Watch your speed. If you jacknife the trailer will detach, and you will have to reattach as in the Tanker Commander mission. You only have 60 seconds to do it and it's even worse if the cops are bothering you at the same time.
For the illegal deliveries, it seems to help to start at night. Also, stay off the main roads if you can, sticking to backroads, dirt roads, railroads, and grass as long as it's flat enough. If you are lucky you will get a delivery of illegal goods that's not too far off the rail line.
The cops will try to drive up alongside you and hit the hitch, detaching the trailer. Speed up or slow down to make them miss. You can also force them off the road or off a bridge. Be careful with head-on collisions as they can jacknife the rig. Don't stop with the cops around or they'll pull open the cab door and arrest you. You can get out of the rig for a limited amount of time and shoot it out with the cops. Just the staties, though; the FBI guys are hard to kill.
For the last illegal delivery, the railroad trick won't work. The tracks do enough damage to the truck that it will explode before you get to Las Venturas. You have to run the gantlet.
There are different cash rewards for each level passed:
After Level 8 the asset is unlocked, yielding up to $2000 per day. You can still make deliveries afterwards, which will vary in distance, difficulty, and reward.