Something I've noticed over the years - much like the exhaust backpressure myths ("you NEED backpressure for the engine to run right!!", when the truth is that you need to maintain velocity), there seems to be very few people that really understand the thermodynamics as it relates to radiators, heat transfer, and how to size radiators/coolers along with "when do I need more?"....so you'll get a lot of "just put it in, it can't hurt, shove the biggest one you can in there". Which aren't necessarily wrong, but don't answer the question either.
The simple answer to "when do I need the extra cooler?" is - "when you're experiencing fluid overheating/burning", which often shows as either smelling burnt fluid, or the fluid boiling/overflowing the cap. The hard side of this is that much like automatic trans fluid, once you've reached that point, the damage is already done. The harder side of it is - how many people have the ability to monitor fluid temps in real time?
You can get a rough idea of how the system is running with one of the cheap non contact thermometers. Go out and run the truck hard down a technical trail, stop, and shoot temps off the pump, resevoir, steering box, and lines in different spots. The usual, absolutely top of the scale temp, you'd want to see is 275*. Chances are, even without the cooler, you won't be coming anywhere near that. For me, if I start eclipsing 200*, that's when I start thinking about dropping an aux cooler in. That's also when I start looking at the system as a whole, as things like kinked or collapsed lines, or other restrictions in the system can also significantly raise the temp of the fluid due to excessive pump pressure. I'm generally not seeing high temps, even in my crawlers or any typical daily driver. Now when I get the 4K pound camper loaded up on the big Ford, and start running it down a trail, then yes, the temps can rise real fast due to the additional weight load on the truck.