Here's a couple of photos I took of how I installed my transmission cooler. This method allows the fluid to run through the factory cooler in the radiator, then through the aftermarket cooler, and return to the tranny. The beauty of this is that instead of replacing the entire return line if you want to go back to stock configuration, you can take off just the "hard line" from a salvage yard truck with an 11/16 wrench and a "quick disconnect" tool.
No - I don't have a tranny temp guage. I did this mainly because the tranny has had to be rebuilt twice in 60k miles, it only cost me $46 for the cooler, and I figured it sure wouldn't hurt! The cooler is a Flexalite rated for 16,000 lbs. They have smaller and larger ones, I rarely tow anything so I went for the middle size. I live in the suburbs of St. Louis and have about a 22 mile drive each way to work - city and freeway. I imagine from some of the other posts I've read that the temp dropped 20 degrees or so.