We have a jeep wrangler. Some aspects of towing may be a little different but for the most part, it is the same...
When we stop for a break or gas, we check our jeep. Takes a minute to walk back and look. Over 18K miles, we have had a safety chain come unhooked and the 7 pin come unplugged. Had we not checked, we wouldn't have known of the problem.
We both do the pre-check separately, double checking each other's work; sometimes in haste, one can overlook something. We are both capable of hooking and unhooking alone; you just never know when it may be necessary.
If we are overnighting in transit, we just leave it alone. There is a greater chance we would forget to redo/undo something than for something to happen while parked.
Hope that helps!
