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So which of the outlets on the transmission is the outlet and the inlet so to speak?

Front is outlet and rear is inlet, as far as the cooler, it really dont matter which you use as inlet/outlet, mine is long and narrow sitting in front of the radiator, the heat rises therory is correct but with most addon trans coolers that dont go thru the rad cooler first it makes absolutly no difference in cooling effect.

Light travels faster than the speed of sound,,,this is why some people seem bright untill you hear them speak.