I have ran upon a similar problem and am in hopes someone has had so experience with the drop tail utility trailers.
I am tired of knocking off the fender mounted lights that are set so low the catch anything and everything.
I just purchased a rather tired and rusty but very solid little 4 x 8 flat bed utility trailer ( for $200.00 ) with the air gate
for the gal pals ZTR lawn mower.
I am hoping to mount the lights on the underside of the air gate. This puts the lights at a bit closer to eye level and may
make the trailer tail lights more noticeable.

I see three problems
1. Protecting the wire while getting it over the vertical square tube that supports the expanded metal.
2. the hinge point from under the trailer bed to up the drop tail.
3. mounting the lights in some manner that will not have bolts sticking thru the expanded metal and
thus pointing upward when the ramp is dropped.
I am sure the wire can be routed thru some EMT or PVC piping to protect it on the drop gate. And even
when dropped the lights are held up high enough to be protected from the ground. Seems my biggest concern would be having the
tail of the trailer come into contact with something like a curb that may slice the wires. It is like I need a solid tube fitting that
is hinged or can articulate at least 90 degrees.
Any Ideas ?