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(physical limitations permit me to drive only one at a time)---
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LOL, I have the same condition.

Yea the driver should be the one who is insured with PLPD, not the car. Worst case scenario take the car which has the worst rating and charge that rate, and only that rate. Then again that is to logical.
Well my two can't tow each other, and the law in my state states that the towing vehicle insures the equipment being pulled behind it.

Who knows maybe this is different for another car, but for a trailer it holds true. Jump starting a car, they both stay stationery therefor no property damage could be done.