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Do you have any friends/family who are up for an adventure? We have a friend that is willing to be the extra driver for the truck (and to keep my fiance entertained) on our 1,600 mi move in a couple weeks. We're all in our twenties, but he's willing to join us if we pay for his food (and likely beer!). He's lucky though because as an airline pilot he can fly for free to meet up with us and then go home. I'd much rather pay a friend all expenses and for them to have a trip then have a stranger have anything to do with my move.
I'd be very wary of letting anyone I don't know drive my car or a truck I rented in my name. Have you thought of shipping a car to free up a driver? Or, towing it behind the truck? Not sure what your set-up is, the size of your family, or how many drivers you have...
For 5.5 hours, if you had to make more than one trip it wouldn't be out of the question, especially if you could space out going back for the other car at least a week.
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