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Around here, we see all kinds of odd combinations on the almost empty roads. Assuming a normal tow rig, the van does all the steering, and only needs the car brakes in an emergency. Extra caution would probably keep the risk to normal levels, except for official interest in the legalities.
The combined mileage is hard to predict, but I'm sure the best option would be a trailer that works as a tapered tail for the van, with sliding panels across the gap.
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