In the 7 years I've owned my Jeep the only thing that broke was a sway bar connector. Heck, I'm still running my stock rear brakes. I drive it everyday, it is my ONLY vehicle. For now. Soon it will become a trail rig, and then ALL bets are off.
Your insurance rates will depend on your driving record. I used to drive a 95 Monte Carlo in another life, and the insurance for my Jeep brand new, was about the same. Now that I'm older than 25 it has gone down even more. I think I pay about 65 bucks a month for full coverage. I have no accidents on my record.
knock on wood.
Also, I don't know where you are located but if you're looking for a new Jeep, I'm in sales at a dealership in PA. We can drop ship to any dealership in the U.S. Just FYI. I'm not a pushy SOB or anything. Well not usually. lol