Clive,
You bit off more than I can chew in a single post, so I'm going to try and hit the high spots, and hopefully you can tell me where you want to dig deeper.
First, the math really doesn't have to be terribly complicated. In aero we frequently use models that are perfectly rigorous, without getting into unneccessary detail. The way we model a wing for example is to characterise it's lift to drag ratio, its span, aspect ratio, and overall coefficient of lift. This will tell us most of what we need to know about a wing for most of our purposes without having to solve the simultaneous Navier-Stokes equations using computational fluid dynamics codes. We can take a similar approach with the prop cart - and delve deeper only if desired.
There are really only a couple of imporant parameters needed to characterise the cart: advance ratio and overall efficiency (if we neglect scale).
Whether we are talking about pulling a yo-yo by the string, or putting this cart (
http://www.putfile.com/pic/2794071 ) in a tailwind, or analysing the prop-cart, the advance ratio tells us whether the cart will go downwind faster than the wind, or it will go upwind - and how fast.
The advance ratio is simply the theoretical ratio of speed the cart moves through the air (or string in the case of the yo-yo) divided by the speed it moves over the ground. For the prop cart this is the distance the prop would theoretically advance in a single rotation divided by the distance the wheels would travel in the same single rotation of the prop. It is determined by the prop pitch and the gearing (including wheel diameter).
If the advance ratio is less than 1.0 we have a cart that will go downwind faster than the wind. If the ratio is greater than 1.0 the cart will go upwind. As the advance ratio approaches 1.0 from either side the theoretical speed of the cart will go to greater multiples of the wind speed (upwind or downwind). At 1.0 the answer is undefined (it would be infinitely as fast as the wind both upwind and downwind at the same time - doesn't make much sense).
However, moving the advance ratio towards 1.0 is exactly like putting your car in high gear. You go faster, but you have less guts to climb a hill (or overcome real-world losses). This is where the overall efficiency of the cart comes in. We lump prop efficiency, transmission losses, aero drag, and rolling resistance all into this parameter. The more efficient the vehicle, the closer we can make its advance ratio to 1.0, and therefore the faster it can go - either upwind or downwind.
Now onto the math...
There are a number of ways to approach the math without getting overly complex. I think the most obvious approaches involve energy balance, or force-vector diagram. I find the force vector diagram more compelling, but both certainly have their place. In the case of the force vector diagram it's far easier if we unwind the path of the prop tips and look at this path in two dimensions. From there we can easily show how it winds up to produce the DDWFTTW cart.
If one or both of these approaches are of interest, just say so. I'll be happy to see if I can make them clear.