aggie79 wrote:...How do these thoughts/theories apply for a trailer being towed in the "disturbed air" behind the tow vehicle?
I think I can be a bit more helpful than the answer above, where I just punted to a rule of thumb.
Here's a great image of a tractor trailer rig showing the contributors to drag

It shows what's important for a tow vehicle with a trailer.
The front drag depends entirely on the tow vehicle , the trailer plays no role in that 19%.
The 14% drag contribution by the gap is interesting. It's probably worse for a typical automobile with a teardrop, because the gap is bigger, and the trailer roof is relatively taller.
But the closer the trailer gets to the tow vehicle, the more we drop that component of drag.
The under body and side drag components are probably more important for big semi trucks than for a jeep with a teardrop, because the semi truck is just so much bigger. Far less skin drag and under body drag on camper rigs.
That 33% base drag component is the part we are really talking about here. If we fill that region with a tapered teardrop trailer, we get some benefit.
Now here's the only image I could quickly find for a modern looking SUV type tow vehicle. It's from an SAE paper by engineers at Jaguar looking at the effect of bleeding air from the high pressure in front of the vehicle to the low pressure region at the back. I honestly can't tell if this image is with or without that bleed air.

That red region is where a perfect trailer shape should fit to really reduce drag.
We see right away it's a pretty bad shape for a practical trailer. Too small and short and low to be comfortable.
But if you are truly interested in reducing drag and increasing fuel economy with the trailer:
- get as close as you can to that shape
- keep the trailer tongue as short as you dare so it's close to the tow vehicle
- keep the roof of the trailer low so it's not higher than the roof line of the tow vehicle
All the above discussion ignores vortex shedding and the associated drag from that phenomena.
My take away is that a smallish teardrop ain't so bad for aerodynamic drag and fuel economy, and a square back trailer costs some additional fuel economy to get that nice usable space in the back of the trailer.
That aerodynamic shape I posted above in this thread looks to me like the Schlörwagen, a 1939 German aerodynamic concept that is among the sleekest ever designed. Notice that it's not prismatic, with straight slab sides. It's also rounded port-to-starboard, like half a jelly bean.
Here's a video of it in a wind tunnel
https://www.youtube.com/watch?list=UU2iaRtEaE3Xbj3wPBot1-ZQ&v=JRfb2-tyRyg