Holy crap Chris, it may be nice but that is a huge chunk of change, and is quite a way towards an actual rebuild.
After digging around I realize that "for jeep" ones are at least double the price if not triple. what is the advantage of those over a $90 one from orielly's?
to OP, there is nothing overly complicated about a trans cooler. It is simply a radiator for your transmission oil. You can go all in like the one Chris posted or go to Orielly's and spend less on a cheap one that will do the same thing.
I've never done this on a jeep, but it was super important to do on the vehicle I used when I delivered mail out in the countryside. 400 + stops over the course of 5 hours on the road tends to annoy brakes and trans. I used the cheapest one from the auto shop in that small town and the effect was immediate and amazing. The install was quick and dirty, so this is not a precision thing. You are just cooling the oil down a bit. I spent $30 on a small one.
The stock way this happens is that it is run through the radiator. This means that it is going to be at least as hot as the coolant. So the aftermarket cooler gets installed after the radiator before it goes back to the transmission, otherwise it is pointless.
So to conclude, in choosing one, take some measurements behind the grill and get the biggest one that fits. width height and depth. There is no reason to break the bank.