I use to be in sales and I can tell you that there can be a HUGE difference in price between two vehicles that are the same year and with options and equipment.
When I went out to buy my Ram it was about finding the right truck. I was willing to pay way more for a truck that was a total cream puff / 8. 5-9. 5 out of 10, the 10 being new.
So what I'am trying to say is it all comes down to mileage, exterior condition, are the seats punched out, has it been smoked in, any foul odours etc. A really really clean truck with the right interior, exterior colour combination with very low mileage can pull way more money than one that's the opposite, as much as double the price. When you have a truck like that or any vehicle for that matter, you can hold out for the big dough. If the first guy doesn't buy it, there will be someone waiting around the corner that will buck up for the premium piece.