I have loaded 3 machines in 16 foot, but is not something I would like to do on a regular basis. A 2 foot overlap is not as bad though. You can back one machine in then put in a bar that goes from one side of the trailer to the other that you hang ramps off of. Personally, I would want to be able to drive the second machine in and up the ramps with the tires dropping down a little once in far enough and not be able to drive too far.