Here's my tale.........
I had my DTT mods done in October of 01. Temps never seemed to be a problem through the winter. As summer temps got hotter I noticed the transmission temps going up a little. I have the Mag single deep pan, about 2 extra quarts I think.
Anyway I added some fans to the stock transmission cooler on the front. I was able to slow the rise of the temps but not stop them or lower them. When I added the fans I also put a second sender in the pan to monitor the pan temps.
Temps are 150° on the line in normal driving. Pan temps are about 10° under this. After pulling up to a light the line temps start to rise quickly, typical stop light yields 180°, yet the pan temps barely change. The worst I've had on a hot day was line temps of 210° and the pan only climbed 10°. Turning on the fans slows the process down. I wouldn't spend the money or time again.
With your double deep pan I would guess that the pan temps will climb even slower due to the extra fluid. Unless your temps are going way higher than these I wouldn't sweat it.
Garrett