First, look for the most stock jeep you can find
a street queen
look for a vehicle that has not been altered at all
no lift, no engine changes etc
in other words look for a jeep that has not been abused off road or is a project some one cannot get right.
avoid any Project that is unfinished, infact run like hell from any unfinished project
avoid any jeep that has a large lift and looks like it has been abused
avoid jeeps with "sweet drive train changes" such as It has a chevy v8 or a this or that tranny, Conversions cost a mint and getting rid of one is because it does not work.
first thing to look for is body rust, especially the floor, then look under the body t the frame, do not be afraid to knock around with the handle of a screw driver for rust, if he complains, walk off he is hiding something.
when under the jeep look at the condition of the drive train, leaks, abuse, bends etc in the axles, drive shafts,tranny,t case, engine, oil pan dents.
if that looks good, get in and start it and check the steering for looseness and wander.
then look under the dash for splices in the electrical system
then look under the hood at the wiring and the condition of the air filter.
all the time during this the owner is going to be trying to sell you a Jeep, his practiced speech is going to try to direct you to this and that, do not say much to him, just humph and hummmm, looking at him with a strange look every once and a while and looking puzzled. Once you are convinced he is not trying to put one over on you, and having ignored everything he asked you to look at, look strait at him and tell him the jeep looks rough, and how much will he take for it. Never make an offer, when he comes back , if it is too much then hand him a card with your cell number and tell him you need to think about it. Tell him he can sell now, or he can wait till later, run your fingers over the wad of hundreds in your pocket and tell him to give you a call when he is serious.
bet you will not get out of the driveway before he discounts big time.
never give an offer, never agree with him, never follow his lead, you need him to be off balanced, it is called horse trading.
PS, I can buy a street queen here in SoCal for around 3 to 4 grand all day long. and the price goes up and down depending on condition. Lifts, equipment and accessories are not worth anything as you will probably end up changing it.