This one can actually be cheesed pretty easily.
Select the Island map.
Clear the map with watch points.
On this map there should be a D-535 to be found.
When you have this vehicle take it back to the garage.
Set up the B-130 with a small lumber load attachment.
Using the D-535, winch the B-130 to Log Station to the South East.
At this point:
Load the B-130 lumber.
Winch the B-130 to the D-535 via the D-535.
Follow the trail along the shoreline to the Lumber Mill to the South West.
Switch to the B-130 and unload.
Return to the Log Station and repeat 3 more times.