I've got a 2000 TJ and I can tell you overlanding works, but it's tight. Wife, two kids, and me in the vehicle doesn't leave much room for gear. I've got a roof rack and/or tail gait basket depending on how much gear/toys we're bringing. Here's a pic from a summer trip where we were out for 10 days and brought inflatable paddle boards, backpacking gear, cooler, etc. I'm aware my packing job looks like the beverly hillbillies, I had just installed the roof rack 3 days before the trip. I've refined it a bit :).
I love my TJ, but I'm not convinced it's the best vehicle choice for overlanding. That being said, I have absolutely no plans to change anytime soon. I'm a big fan of dancing with the girl that brought you to the dance, and my TJ still has a sparkle in her eye.