Here's the thing in sales.. if you sit on something long enough, somebody will pay your asking price.. may not be this week, or even this decade.. but sooner or later, somebody will come along and pay your price.
Big outfits who put high prices on these trucks are trying to get the buyer into a mindset.. and to be quite honest, their target buyer isn't you or I.. it's the guy with $100,000+ in his 'play money' fund.
They don't really want $29,000 for that truck.. but that's their opening offer price. If somebody comes along and snags it at that price, great. If not, they'll sell it to a guy who offers $21,000.. he'll walk away thinking he got a deal and a half thinking he got the seller to drop their pants 8 large.. but in reality, he still paid $3,000+ more than it was worth.
Setting your opening price high on an item like that automatically eliminates the people who wouldn't buy it anyway.. and saves them from having to bother with unqualified or not likely to buy tire kickers.
My guess is the target buyer for a truck like this at that price is the guy with some disposable income, who really dosen't know what he's looking at.. but sees what they bring at Barret Jackson.
They think it's a neat looking truck, and justify the expence as an 'investment'.. with purchase and apprasal value being set high, they have themselves a tax write off when they sell it and loose money.. plus they have a neat old truck in the garage to show their friends.