lol i saw your ad. $5k is right at the top of my price range, and the last time i was in colorado i DESTROYED my jeep hahaha.
anything in particular to look out for with these things? obv you can tell if it has been maintained or not, but any weird items like the 44 whining?
In the overland, the biggest thing is the blend doors in the electronic climate control. The late production 2004's don't have this issue. Mine didn't.
Other than that, the heads will drop the valve seat if the thing is overheated. The coolant is a 5year 100K hybrid organic additive technology (hoat) fluid, and anything else will cause corrosion and cooling issues. The coolant tank up near the passenger side dash should be a healthy pink color.
The power steering and tcase fluids are WJ specific, for the steering it is a mopar fluid because it has a connected hydraulic cooling fan. The tcase fluid is mopar only also, because of the viscous coupling in the 247 case.
I'd interrogate the seller for maintenance and repair info, those are things you don't want to skip.
Rust is common at the spring perches, because the isolators trap water.
Other than that, the older models have rotor issues but that was largely fixed by 02. The 02-04s can be used with the superchip tuner, the easiest way to make major HP, torque and driveability changes. You can also easily change the speedometer reading easily.
When I got my overland, I changed the oil, the pcv valve, fuel filter and did a major inspection of everything, at 89K miles, it is doing very well.