It seems like the head issue is made out to be more severe than it really is, but there really isn't anyway to know if you are going to have a problem or not. If you overheat the 0331 head, it is much more prone to cracking - doesn't have anything to do with offroading vs daily driving.
If you find a good deal on a 2000 / 2001 I wouldn't be afraid to go for it. Just keep the cooling system well maintained and keep the thought in the back of your mind that the cracked head is a potential failure point. There are also some out there that could have had the head replaced with the revised 0331 head. Pop the oil fill cap and look down inside with a flashlight. If you see "TUPY" cast between the #3 and #4 cylinders, you have the replacement head that is not prone to cracking.
1992 Cherokee Laredo - all stock, DD. Needs some minor rust repair, then on to the mods!
1996 Cherokee Classic - 3.5" lift / 31.0x10.5 Mastercraft Courser CTs / Warn XD9000i - Stripped for parts / junked :(
2004 Grand Cherokee Laredo - 4.7, bone stock - Wife's DD
NJ F-Body Owners Association