Just for rOnin89, Jeeps hold their value so well because they are the best vehicles ever. Period. Nothing can touch them on or off road.
Seriously, they hold their value because they are very popular. People love that in the summertime, you can drop the top and go to the beach. People love that in the wintertime, they will be unstoppable in the snow (Or so they think). Plus, the drivetrains tend to last a very long time, whether 4.0 or 2.5. The lower the mileage, the bigger the price tag.
I bought mine new in 2001. Nine years and 149k miles later, I still love it. I used to commute daily in it (Both before and after I lifted it). In 2003, I drove it to Richmond, TX, pulled into my uncle's garage, lifted it and installed some 33s he had for me, drove 200 miles north to Gilmer to wheel, drove back to his place, and then drove all the way home to Jersey on gigantic 33 x 14.5 x 15 Mickey Thompsons. Admittedly not the smoothest ride but I didn't mind it. My wife, on the other hand, could have done without a ride that long.
If you do get one, don't expect it to handle and ride like a Caddy. Despite the coil springs, it's still a Jeep. Also, the more you do to it, the more you HAVE to do to it. For example, if you want to run bigger tires, you're going to need to lift it. Then you'll need longer shocks. Then you'll have to worry about steering geometry. Hence, JEEP - Just Empty Every Pocket. Even something as simple as pulling the doors off for summer means some money out of pocket for mirror relocation brackets or another set of mirrors. It's a sickness.
Good luck!