The primary enemy of the trans is heat, so I would definitely recommend a cooler. The stock cooler in the radiator is immersed in engine coolant, so whatever your coolant temp is the minimum temp of your trans fluid (about 180-195). If you plumb in an external cooler, you can significantly lower the temp and extend the life of your trans.
Another option you might consider, in addition to the trans cooler, is using the Mopar ATF+4 fliud in your new trans. The Mopar fluid is fully synthetic and thus will not break down under high temps like conventional fluid. The last time I was at the dealer I was able to talk them down to $6 a quart, about the same as auto parts store prices.