One topic that I haven't touched on at all in this space is how car salesmen sell cars to members of their own family. Almost everyone in my family has purchased a car from me, as well as a few members of my girlfriend's family.
It's always a sticky situation. You have to take care of everyone involved; the family member, the management, and yourself. It seems like no matter what you do in a family situation, someone always has to sacrifice. Normally, it's the salesman. We get crunched from both sides; the family tries to get a car for free, and the management tries to maintain a healthy profit margin.
Perfect example: My girlfriend's aunt and uncle came in to buy a vehicle. Let's call them Bob and Sue. My girlfriend's father wanted me to take care of them. I did, giving them a deal on a pre-owned Chevy TrailBlazer. The TrailBlazer had leather, seats with heaters and memory function, sunroof, CD changer, and premium sound. I gave them a $2,500 "family" discount, and I certified the vehicle at no extra cost to them (giving the vehicle an automatic warranty). They were happy.
My girlfriend's father, however, wasn't convinced that we gave them enough of a discount. I countered, saying that by covering the certification, we in effect gave them a $3,000 discount. There's no way we would have taken that much off for a normal customer. (A note: Perhaps we might end up taking that much off for a normal customer, but whereas a normal customer would have to fight tooth and nail to get us to that price, I made sure the deal was sweetened for Bob and Sue enough to not have any further discussion.)
Pressure. From all sides. A good deal is a deal that makes all sides happy. It's not something that happens often when family is involved.
It's a little different when you're working on a new car. I sold my father the first Buick Regal in town. There weren't any rebates available on the Regal, so we could only offer a slight discount on the vehicle. We made it up on the trade-in, giving him $500 more that we had appraised the car for. He was tickled, though, because the Regal is a gorgeous car that has earned him a ton of respect and kudos.
In the end, when it comes to a family deal, we salespeople try to take care of our own. It's just a little harder than everyone thinks it is.