To really know the answers requires some very complex computer modelling or some real modelling (using wind tunnels, correct wind speed for the scale of the model so that the Reynolds numbers are correct, etc), or even a mock-up full-sized trailer pulled behind a tow vehicle with a strain-gauge on the coupler. So, it is hard. Here are some rules of thumb:
1) Getting the frontal area of the trailer "shielded" by the tow vehicle can have big impact. Sure, there's going to be turbulence in the "gap", but in general terms, you've already "paid the price" to part the air with the tow vehicle, so the major frontal drag from the trailer comes from the parts that stick out above/outside of the "shadow" of the tow vehicle. This is particularly true if the tow vehicle has a blunt rear (i.e. a panel van)--a sedan with a trunk and a more "streamlined" rear end will not provide as much effective shadow area.
2) If air is forced to turn a sharp corner,it will become turbulent and often will increase drag. This is why even a small (e.g. 2" radius) corner at the top of a trailer is preferable to two sheets coming together at 90 degrees.
3) The rear of the trailer can contribute as much or even more drag than the front. In the link below, they say that, for a typical tractor-trailer rig, the front of the truck accounts for 20% of the drag, the skin friction is 5%, and the rear of the trailer accounts for 25% of the drag--so, more than the front of the truck. (The remaining 50% comes from drag underneath the truck/trailer, which is why we now see front and side "skirting"). In simple terms, when the air flows past a sharp edge at the back of the trailer, it creates a low pressure zone there (a "partial vacuum"), and this "pulls" the trailer back. If we could have a true teardrop shape (a streamlined airfoil) and keep the air attached the whole way to a sharp tail, this would significantly reduce drag. Unfortunately, that usually makes for a very impractical trailer shape. Still, even giving the rear of a flat-back trailer a minor "boat tail" using the actual shape of the body or with panels that can fold out of the way can significantly reduce drag. We see these sorts of panels on commercial trailers, and they do reduce fuel use. For details on various configurations that have been tested, see:
http://people.clarkson.edu/~kvisser/res ... AE_365.pdf. The details of these panels (size, angles, inset from the edge, etc) don't appear to be very critical, so just an eyeball approach is probably good enough for our purposes, and might produce observable improvements in fuel economy for a square-back standy trailer.
4) If our vehicles are at least somewhat similar to commercial tractor/trailers, then there might be a lot of drag reduction to be gained by aerodynamically cleaning up the underbody area (as noted above--older trucks had 50% of their drag here). But, there are obviously practical limitations--skirts, air dams, or anything else that reduces ground clearance will also reduce the number of places you can take the trailer, etc.
5) It's important to keep all this in perspective. For most of us, our trailers aren't being pulled all day, 98+% of the time they aren't moving. And when we are using them to camp, they need to be practical and we need to be able to us the space inside them. Even a super job of reducing drag might improve our fuel economy by, at best, a few MPG, which really doesn't amount to a great deal to most of us over the course of a year--obviously things might be different if the trailer is pulled at 85 MPH for 12 hours per day and it is just a place for sleeping on rapid cross-country cannonball runs. But if we assume a trailer is pulled 2000 miles per year, fuel is $3/gal, and mileage goes from 20 MPG to 22 MPG, the difference is just $28 per year. So, the payback period for any drag reduction expenses might be a very long time for the typical user.
Mark W.