I used to have a wrangler. It was a piece of crap but I loved it.
Considerations:
Who owned it? Is it well taken care of? Check engine especially. Jeeps have a tendency to get beat the hell out of. Check mechanicals very carefully. Clutch system is worth a good check too.
Definatly find something used, in good condition and with some good upgrades. Aftermarket parts don't really add any resale value untill you get into major suspension/engine upgrades. You can get good tires, rockerbars and all sorts of other stuff on it. Check accessory sites to get a good idea of which parts are cool and which suck (floppy mirrors believe me). Jeeps are the most accessorizable vehicle I've ever seen.
Keep in mind that they're not great on the highway, and they're rather small, but newer ones will go well on highway, except for gas milage.
Even with accessories, don't pay more than 5-7,000 for it. Unless it's super new with low milage and good stuff included. Even then, you can find a good used one (even CJ) for around that price range.
Soft tops are good but parachutes on the highway. Also kinda cold in winter. Hard tops are cool for winter, but soft top is divine in the summer. (You never get locked out with a soft top)
What other vehicle can pop the doors off, drop the top and still turn a complete circle in a residential street? For added pimpness when cruizing, get aviator goggles and put windshield down.
MOST DEFINATLY get a manual transmission!!!! Automatics are 3 speed and a bastardization of what a jeep really is. Dont be lazy, get a stick! They are very very easy to push start with two people if you have a stick.
It WILL be 4x4 (all jeeps are) but locking hubs (rather than static as are stock) will greatly improve gas milage.
Keep in mind they are top heavy like any truck, but not bad. Just don't slam it into turns.
Want a radio? Either get a sound bar, one of the other speaker boxes or screw regular 6x9 boxes to the wheel wells like I did.
Riding chariot style offroading with a trusted driver and the top down is awesome!
When my fanclutch went out on my inline 4cyl, we took it off and my friend was standing in my engine compartment! Lots of space to work on it (older jeeps). Good do it yourselfer.
Dont get an inline 4cyl, get a 6cyl. (capable of fitting V8 with good mechanics help, but this is overkill)
If you want to offroad, get a winch, or find one with it on there already. Grill guards are important too. I personally perfer the Euroguard (no idea why that name).
No dome light? I reccomend an A/C converter and christmas lights for that festive look. Roll bars are so multifunctional. (.30 cal MG doesn't hurt either, and tends to help with traffic. Obviously kidding here, and not sure about legalities, but you can actually buy a semi auto .30 MG for $1100-1600, check gun broker)
Camp Jeep looks like fun, check it out!
Deliver pizzas? Car toppers sit well on the hood! Belive me! Pizza place got those old window flags? Go for the staff car look with the hood clamps! This is a lot of fun too.
Stock jacks suck and won't work with a lift kit. Get a good heavy duty one.
For offroading at night, lights on top of windshield are best. They shine over the hills, think line of sight.
Most importantly: When you get a jeep, always execute proper jeep wave when passing other jeeps!!! Either extending fingers above wheel or sticking hand firmly out open (gaping open) window. Havn't seen it before? Belive me you will. One of the best things about a jeep is the community. Its a jeep thing, anyone else just wouldn't understand.
Damn I love Jeeps (even though I now drive a Tacoma).