The prices quoted in KBB are an average of all reported transactions for same make, model, year, comparable mileage, factory optional equipment, overall condition, etc. Usually given as retail (what a dealer charged), trade-in (allowance given in trade), wholesale (out the door to get rid of it via low-end dealers or auction houses). In recent years there may be a value quoted upon private party resales (no dealer involved).
What I have experienced is dealers who focus trade-in only on the "base unit", regardless of factory upgrades that increase value, and understate potential value due to overall condition, low mileage, etc.
Naturally, since the buyer is focused on something he wants to acquire, the emphasis is heavily placed upon the ultimate desirability and value of the unit picked out by Mr. Customer. Also, since the buyer wants to trade in a vehicle no longer wanted or needed, the emphasis is heavily weighted against that particular unit because of low market demand.
In the military we referred to these things as psychological operations, tactical maneuvers and information intended to persuade the other side in the decision making processes.
Of course, the tag team approach comes into play as the sales rep, sales manager, and finance manager take turns on Mr. Customer, blow smoke, pump ego, deflate willpower, inject doubt, generally convince Mr. Customer that it will all be much better after he has signed the papers.
Dealers and sales reps don't even want to talk about price, all they want to know is what level of payment you want, then try to build a deal based on that. Even when they pull out the dealer invoice on the purchase intended that really tells you nothing, because those figures are constantly in flux depending on dealership volume, factory incentives, and a dozen other undisclosed factors. The factory invoice is nothing more than a gimmick by itself.
Many people purchase a new vehicle several times during their lives, and many prefer to trade in the old vehicle rather than deal with the hassles of selling it privately. Very few people spend the months and years necessary to perfect the negotiation techniques common to modern car dealerships.
Caveat emptor.