Get a gooseneck trailer rated at 9,990 lbs. Put 3,000 lbs on the toung, the trailer should weight in around 3,000lbs as well. This will let you pull a 10,000 lb machine legally. The trailer rating is for the axles and this will work as long as you are under the GCVW for the truck and under the axle rating or the truck.
I've never been skydiving, but I have zoomed-in on Google Earth really fast.