It's actually gonna end up being trial and error on your part. Your gonna want to place everything to where you have the trailer balanced correctly. Not all the weight on the front, or behind the axles.
On my 16 ft trailer, when I picked up my l1501 and brought it home the first time. I had the tractor, back blade and bush hog. We ended up backing the tractor on with the back blade. Dropped that and stood it on end against the rails. Then hooked the bush hog on and drove onto the trailer with the bumper locking the back blade in place.
That being said, I had a little too much weight on the tongue so the front of the truck was pretty light. The 30 minute drive home took an hour with me getting the occasional 1 finger solute
For my tractor, it handles the best with just one implement on the trailer and the tractor backed on. With the front tires on the edge of the dove tail.