The only way I'd buy a used car is if i knew why it was being sold -- if a friend makes a lot of money and wants to sell a 5 year old well maintained car because he's buying a new one, sure. If someone has an S2000, has a kid, and needs something with more seats, score. Otherwise, adverse selection seems to be a big deal.
Yes, and I wouldn't trust a story of the provenance of a car/reason for it being sold if it were NOT being sold by a friend.
Also, my friends maintain vehicles well, which is a major factor in their survival past 100-125k miles with minimal ongoing maintenance. I like cars with turbos, high compression, etc., so it's a bigger deal.