your question opens a can of worms
so many opinions
however this is me and my plan of attack
last year when my truck was new to me, I ordered a cooler and bypassed the radiator
however...I live and work in cold winter climates ( 6 feet of snow, low 20 is a winter norm, I'm expecting worse this year, we have had 16 feet)
a few days ago on a steep back road I saw extreme trans temps ( well to me saw 237)
so I am worried about not only running hot but running cold
so today I ordered a new radiator, thermostat, and other stuff and I'm going back to "in series".....first to the radiator then to the cooler
so that I don't get too cold this winter, and I will see how it goes this coming summer
if crawling next year I heat up, I will add a pusher fan on the trans cooler
but like I said...your question opens a can of worms