Free your mind of the compromise made to keep using the radiator intercooler.
Bypassing the radiator removes the risk of coolant getting into the transmission. I have paid for several transmission rebuilds from the radiator intercooler tank getting a pinhole leak. The leak is so small that fluid changes just about cover it up. Aside from doing oil samples on the transmission that I have not done in the past the only sign of this pinhole leak is rust appearing on the top of the trans dipstick. Water dissolves the glue used in clutches and coolant mix rusts bearings. Till they lock up and spin costing extra to get the bearing support in the case welded up and re-machined on rebuild.
Putting the air to oil external trans cooler in front of the condenser adds heat to the stack, but, gives the cooler constant airflow because the clutch fan is always moving air at its 20% lockup minimum. Put the biggest cooler you can fit in front of the radiator and you should be fine. Out here I did this and had no issues towing with my Yukon on the rebuilt trans from pinhole leak radiator - and I did not have to replace the radiator.
The radiator acts as a surge absorber from the transmission for it's only benefit. This heat surge has to go through the engine before it reaches the cooling section of the radiator. Getting really hot will put bubbles to the intake of the water pump and cause cavitation. Say your OD has failed and you are running direct,3rd, to the trans shop for a rebuild and the trans temp gets over 240 like it did for me. Radiator only intercooler alone is simply known to not do the job when you put a heavy trailer on and put the hammer down. (esp. like you have to on a 6.5 towing.)
When cold the radiator intercooler does not warm up the transmission. Depending on what you are doing the transmission can warm up the engine from a cold start. If the radiator did warm up the fluid why does the fluid then go to the air to oil intercooler? Simple, to get the coldest oil possible back to the transmission. This is a cooling circuit not a heating circuit.
In the end you want to get the heat out of the transmission to the air. Using the middle man of the engine's coolant gives you losses in efficiency.
As far as electric fans on the cooler I suggest the KISS method. Power the fan with the ignition. Let the cold fluid bypass do it's job and avoid the expensive temp switch. The switch is one more failure point and 2 connections. Plus you can test the fan at key on and know it is working: not jammed with a rock or failed.
As far as 6.5 experience towing flat out on the 7% grades to Payson,AZ and beyond I am not happy with the use of both coolers: an air to oil and the radiator intercooler with radiator first in the hot oil flow. This is where you find out that engine temperature and transmission temperature are independent. Engine can be reaching 210 and the trans can be at 180. Forced to 3rd without the TCC locking up the trans can hit 220 and the engine below 210 with the fan screaming. I learned to let off the throttle and back into it to 'trick' the computer into locking the TCC. This would allow me to pick up a couple MPH vs. a unlocked TCC. A TCC lockup switch helps trans heating more than coolers can.
My trans shop says the 4L80E runs hot. So the above is acceptable, but, not the best.
Another vehicle I have with a larger, thicker, radiator installed still burned up the transmission with only the radiator intercooler in use. So risk coolant in the trans and it still doesn't do the job...
Climbing the grapevine with a sedan - pried the trans filter out in chunks from heat making it brittle. Added a truck size trans cooler and never had an overheat problem again.
I would use a trans temp gauge to evaluate your results.
If, in fact this is how the cooler is plumbed from the factory, then in extreme cold the trans fluid would gel or get too thick to flow. There is no type of thermo bypass from the factory ,that I know of.
Factory air to oil coolers have the bypass controlled by viscosity.
Quoting B&M's site:
feature known as “Low Pressure Drop”. The coolers assembled with hose barb ends include a unique bypass feature allowing a controlled amount of ATF to bypass the stacked plate core when the fluid is cold. This is beneficial in cold climate areas to guard against lube system failure. Controlled by viscosity, fluid is returned directly to the lube circuit through bypass openings in the stacked plate core. As the temperature increases, more ATF is directed through the core. This highly efficient design combines improved protection against lube system failure with the required levels of optimal heat transfer.
http://www.bmracing.com/PRODUCTS/Au...on-SuperCooler-rated-at-14-400-BTU-11x6x1-1-2