You can't compare KBB to Jeeps because they are a Labour of Love. Money and time go into them that never pays back. So instead of selling my TJ just to get rid of it for $10k, I would rather keep it and sell it for the right price to the right person that understands what transformation it has undergone. 98' TJ KBB is around $9k. However I have receipts totaling over $42k in after market accessories, upgrades and labor (from me and previous owners). KBB is based on a stock vehicle. If someone changes the axles, gears, adds lockers, transfer case and so on it becomes a custom 1 of a kind the the sellers mind. There are plenty of great deals to be had out there and it's usually going to be from the person that either doesn't know what they have or are sick of owning a money pit that won't yield a return on investment, or the guy that never changed the oil.
I look at it as a rental fee on every thing I own. I can't take anything with me when the grim reaper comes calling, so if I spend money on something and come close to breaking even, or lose a little $$ when I'm ready to sell, but get a lifetime of enjoyment and memories to share with people I love, then it's worth every penny spent and lost on it. My TJ is worth what someone is willing to pay for it and it's also worth what I decide to sell it for. I may drop the price $2k-$3k if the right person comes with the right money at the right time. If you are going to low ball me at least patronize the work that has gone into it, don't belittle the rig while looking at it because you'll insult me into kicking you out of my driveway. YES I HAVE DONE IT BEFORE WHEN SELLING SOMETHING. So if you come off with an attitude that what you're looking at it is an over priced POS then maybe you should go buy a brand new vehicle, spend countless hours researching what is the best way to build it is, pay someone to do the work or invest countless thousands of dollars into tools and machinery to safely install the correct upgrades and feel the pride when Super Dad in the stock mini van at the gas station says to you " Dam, thats a sweet Jeep, I bet you can take that thing anywhere ! Have you done the Rubicon in that thing ? " and your reply will be filled with pride when you say "Thanks, yes I've done the Rubicon and have seen parts of this country people never new were here."
Every time I get back from a trip, I amazed of what I just put my TJ through. 75MPH on the highway for 2-3 hours there, climbing rocky mountains, sand washes, climbing over boulders the size of VW Bugs for 5-6 hours and then on the way home again for a 75 MPH for 3 hours of WOW!!!! what an amazing rig. I just punished this thing and it loved every minute of it. Clean it up check the fluids, and it's ready for next journey.
So in closing my sleepless rant, you're not just buying a used car. You're buying the experience of a Jeep, you're buying an elite membership into a club of people that love what their Jeeps can do. You're buying memories for yourself and your family to share for the rest of your lives. So either buy a used jeep that's been built and get out and use it, or buy a new one and sit at home on the weekends and build it. Then you'll know why Jeeps hold there value. Because their owners value their Jeeps.