I've got a 2005 TJ. I wheeled it for a couple years basically stock (31" BFG ATs) and had no real issues. It was capable, rode well, and was just fun to drive.
The minute I put a lift in, I started running into problems. Each fix seemed to cause a new problem that required another upgrade. It now sits on a 3.25" lift, locker in the front, lsd in the back, 33" MTs, adjustable this, unbreakable that, etc. It looks cool, but my wife doesn't want to go anywhere in it. (neither do I to be honest)
Anyway, I guess the only feedback I can offer is this.
Have you come across any trails or obstacles that you really want to do but can't do now?
If not, maybe leave well enough alone and spend the money on beer.
Good Point - stock hasn't let us down yet