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I usually make an evaluation of the person, and how serious they are, and then make a decision.
But in general, IMO, you have to let people drive the car (with you in it, of course) for them to evaluate it and make a real offer. Yes, there are risks to that, he could pull out a gun and kill you, do a money shift and blow up your trans and bend your valves, etc. But at the end of the day, there are risks you are going to have to take when doing a private person to person sale.
I have to admit, I do get annoyed when I go to look at a used $15,000 Porsche and the guy acts like it is a Carrera GT or something. I'm a serious buyer, I need to drive the car to evaluate it, and I don't like being jerked around with bizarre conditions and hoops to jump through to test drive some 25 year old used car.
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