Welcome to the forum! I'll let others answer about the price of a Rubicon, since I don't have one, but welcome.
Some general thoughts:
Stock is reliable (relatively). The farther you get from stock, the more you have designed your own reliability. I don't care what anybody says; lifting or creating more power is less reliable than stock. If you want to replace every single component with a stronger aftermarket one, you'll still miss something until it breaks.
Off-roading is expensive. The tougher the trails, or the faster you go, the more expensive it gets. A lead foot needs a gold wallet.
The more you can fix yourself the cheaper it gets.
Stock rubicons with an aggressive tread are deceptively capable. You won't be a youtube star, but you'll get more places than you might imagine.
My dad always said he never sold a rig that didn't need sold. That's not to say you can't buy a good used rig, but expect to find out early all the stuff the previous owner didn't want to take care of while they were planning to buy another one. It may seem worse than it is at first.
You shouldn't go wheeling alone, at least until you've learned everything it takes to get yourself out. At least take a mountain bike. 20 miles of gravel is a day's walk, or a 2 hour ride. Around where I go, a .45 and $100 will get you a ride to town, a rescue, or both. Just the hondo might do it, but you risk losing it.
Since you shouldn't wheel alone, maybe you should try to find guys that go wheeling in your area, then ask them where to get a good used rig. Just a thought; I've never tried that method but it sounds good. Another method is to find an offroad shop and go talk to them. If they're not nice, find a different one.
If you're married, take your wife to look at really nice, expensive new rigs. Act like you're thinking about saving up for that. Then, when you find a used one for half that, she'll be trying to talk you into it. Caution: I've been divorced once. My new wife and I don't share finances, so take my advice at your own risk.
Good luck! I like teachers, and I like jeeps, so I'm rooting for you.
07 WK 5.7 QD2, 4" lift, 33X10" tires, M8000s
ARB twin air,Dual AGM group 49, sliders and skids