I see your point about lining up with the wind, but our trailers are all relatively permanently mounted blocked and chocked in one area and I would have to rent or borrow a tow vehicle each time, so putting the trailer into the wind is not a no-brainer at this particular field. I will make this suggestion to the field owner though, since others use a Wing Rigger and could suffer the same fate.

I have the later version of the Wing Rigger and I'm not questioning the quality. I'm pretty happy with it overall. I'm just questioning one aspect of the design. What would be wrong with, say, doubling the wheel base length? Wouldn't that at least mitigate the risk of a spill in situations where one can't turn the trailer into the wind?

The only downsides I can think of are that (1) it would add a bit to the construction cost a bit and (2) it would be a bit harder to pack in a trailer with a narrow front door.