You can never change the trans oil too often.
When you do the swap, if you can let it drain overnight, lots more fluid comes out if you give it time.
The last three 4.44s I did, the guy would not guarentee the trans, unless I changed the fluids. And to make sure people do, he puts the trans pan bolts in a plastic baggie inside the trans pan!
As for moving the trans cooler I don't think it's worth the effort. If your tranny runs cooler with the cooler out in the wind, than your AC will run hotter, (you are in the sunshine state) if your AC runs hotter, than your rad will run hotter.
Just my$00.02. Tom