2 main problems, and a 3rd as well but will cost you $$$.
1, Your exhaust routing is the biggest culprit. That hot air rising directly into the cooler in a spot in the chassis that is a dead zone for air flow is heat soaking that cooler. Heat shielding on the exhaust will help some but I dont think it will completely solve the problem
2, The trans cooler is too low in the chassis and the fuel cell is blocking the majority of the air flow through the front side of the cooler. If you cut the mounts off the chassis and pivoted the cooler up on the top side more to get it away from the cell a bit its gonna help alot. Granted it wont be inline with your downtubes anymore but id rather have a trans run cooler than have it visually look a certain way
3, I recommend going to the CBR0059. This is what I run on everything. For what you're trying to do with this truck and based off what you're saying about how you drive this thing, that cooler you have isn't enough for the spot you have it mounted in. If you had perfect air flow going to it, it would be borderline enough. Jumping up in size on the cooler as well as going to 12" fans will drop temps a good amount in a area that isn't getting good air flow on its own, combined that with some heat wrap on the exhaust and bringing the front edge of the cooler up a bit you should never have a trans temp problem again.
Changing gearing to alleviate trans temp is just another band-aid fix that ultimately wont do much. Not only that, just the thought of being limited on gearing options because you're worried about trans temps seems ridiculous

it should never be a deciding factor
I dont know if it was talked about yet, but which way do you have the cooler plumbed? Where does the hot side coming from the trans enter and the cold side going to the trans exit?