What temps are you running now? If you can't answer that question, you missed a step in the process.
My advice, since you live in a cooler climate, is to install a trans temp gauge first and evaluate the need... then go with an appropriately sized cooler. I installed a big cooler in my rig back in the '80s. Later, in the '90s, it got a gauge. I found it was way overcooled in Colorado where I lived. In winter, solo, trans temp (measured in the pan) never even reached 100 degrees unless I had a big load on the truck. I towed a 30-foot Terry Manor and also had an overhead camper on the truck... about 18,500 GVCWR... and my C6 still never reached 250F with that setup, even in warm weather. The trick to avoid overcooling (which can create condensation in extreme cases) is a cooler line thermostat. You can then have the larger cooler for heavy loads and warm weather but the air-to-oil cooler is bypassed when it's not needed, allowing the trans to run warm enough. Cheap ******* that I am, my answer was a cover for the cooler during winter (the oil still flowed thru the radiator cooler). The other thing some folks did was to run the hot oil thru the air-to-oil cooler FIRST, then back into the radiator. I did that on another truck and it seemed to bring the trans temp up a bit more in winter. The newer Fords have a built in thermostat that bypasses the coolers altogether until the trans reaches around 100F.