MudRunner

Start off by loading up the map 'Island' on Casual using the map default vehicles. What you want to then do is attach the 'Log Carriage' to the 'C-255' vehicle and drive out of the starting location and take a hard left where you will immediately see a small raised rock to the right side of the path. Position the rear end your 'C-255' in line with the rock so that it looks something similar to the image below.


Once you have your vehicle in place you can switch to the 'A-469'. What you are going to need to do is use the small raised rock as a kinda ramp in order to get on to the carriage of the truck like the image below.


Once you have the Jeep on the trunk, I would advise applying your park brake so that it doesn't roll off the back. Switch over to the 'C-255' truck again and slowly drive off to the right along the shoreline (Be careful not to go too fast as there are many rocks around which may damage your vehicle). Achievement should pop around the time you reach the river nearby.

I did this on Crossing but you can do it anywhere that there is a small hill to load the truck. On Crossing there is a small "bridge" in the middle of the southern half where a B-131 and a C-255 spawned for me. The B-131 had the small log box on the back. Once I got the A-469 in the back of the truck I hooked the truck's winch to the front of the A-469, switched to pull mode, and pulled it tight to the front of the box. This kept it in there over bumps and had the happy accident of also giving me the David achievement as well. Just drive until they both pop.

There is actually a garage part specifically for this. In The Boyg, drive to the far west of the map, just north of the river. In that area is a CAT (K-700, a yellow construction vehicle). Take control of it, then drive to any unlocked garage, and add the Loader attachment. This will place a giant claw to the rear of the CAT. Now simply line up the Jeep (A-469) behind the Loader claw, take control of the Loader, clamp the claw around the Jeep, and lift it into the back of a flat trailer (the Utility Semi-Trailer leaves a perfect amount of room). Set the Jeep down into the trailer, then drive away from the trailer. You may need to use the Loader claw to push against the Jeep so it falls perfectly into place, as I did. The drive the trailer 200m and the achievement should pop.

Side note:. When I did this, I used the utility trailer as described, and the achievement didn't pop even after 400 meters. I went back to the garage, and loaded the Jeep on to the Log Carriage this time. As soon as I released the Loader claw and the Jeep hit the truck bed, the achievement popped, without any driving. Weird.