Thoughts that pop into my mind with this project.
1) Why mount the cooler in that particular position? What makes a more traditional position undesirable?
2) The wheel well space, in the dead zone in front of the tire, and behind the headlight, is a good space. Just be certain the wheel will not contact regardless of suspension travel or wheel turning.
The air is relatively ambiant and not effected by underhood heat. The air can be quite dead so forced air is a must...already covered with the fan attachment.
3) A comprehensive debris shield must be installed to protect the cooler. This shield should also not trap anything otherwise it will likely be filled with sand and other small debris in a relatively short time. I would think making the shield from some sort of rubber belting, like conveyor belt, or heavy truck mud flaps, would work very well.
4) With the fan motor you could run into harmonic resonance in the fender...maybe not, but it should be tested to verify.
5) The T-stat cooler is the best way to go with this kind of system.
I play with a lot of Cobra Roadsters and many of them have straight run oil coolers. Most of the time with the non-T-stat oil coolers the engine oil NEVER gets up to temp even on the hottest summer days. But then, when the cooler spring and autumn days are perfect for driving, the engine oil temp is even less up to temp...causing wear issues and oil contamination problems to be sure.
I have built a few blocker shields for Cobra guys who do not want to invest in a T-stat cooler, but want to keep the look of the cooler.
I have even done a fake cooler on a few Cobras. Cooler, lines, and everything except for literal hooking up of the oil flow lines. Looks "right" but is nothing more than window dressing...and the engine runs perfectly and all temps are safe.
I think your fenderwell trans cooler will work fine if done correctly and thermostatically set properly.
I suspect it will scare a few people when the fan comes on automatically. Especially after shutting down and things are quiet in a parking lot or garage.