I did change the transmission cooler. By that I mean I removed the stock cooler, and put a different one in its place (they occupy the same space just ahead of the radiator).
Perhaps I didn't absolutely need to add a bigger cooler, but I feel better when I see nice, cool transmission temperatures vs. nervously watching the gauge. Anything in my older comments would likely be more accurate, as I was reporting temps closer to when they happened, but I pretty much can't get it over 185º now, even pulling big passes, while towing, in high ambient temps. I would think anything under 200º (occasional) trans temp would be acceptable. Somewhere I have a chart that shows trans longevity vs. temp and basically the cooler the better -- and longer lived.
I did ask the shop what would be too cool. As I remember it they said it should get up over 135º (but if I said something different earlier go by that). I don't have any problem achieving over that on every drive. That' said I don't drive in winter weather with the Chinook so no idea if that would be an issue. (The shop being John Wood where I had my transmission repaired and improved) (I have the 4R100 transmission.)
If I were to do it again I might see if I could find a slightly smaller cooler (but then again this one is tried and true). I went with the one I did upon recommendation by a multiple Ford van/V10 owner who tows heavy. The one "downside" to it is that of course it blocks the radiator a bit more, and throws its heat onto the radiator (as did the original, but it was removing less heat). The result of this is that if I'm towing, pulling a pass, and it's hot out the engine cooling fan will come on a bit more often than it used to (just for a minute or so but you can't mistake that jet engine for anything else). As a result my engine runs just as cool as it ever did; but the fan comes on a bit more often in those high strain situations (typically it comes on as I get to about 200º FWT and then goes off at about 197º which takes about a minute; it will then repeat every few minutes while I'm on my way up a pass or some other extreme maneuver). Normal driving you would never know anything was different (except for nice cool trans temps). I don't think I have ever seen my engine coolant temp over about 202º The fan then immediately comes on and in about a minute it is back to 198º and shuts off.
I figure the transmission is defenseless when it comes to removing heat (except for the trans cooler), whereas the engine does have that cooling fan and can use it. If it happened all the time I would probably look at reducing the cooler size. In my case it's just in hot weather, going uphill while towing, or while running AC and climbing if really hot.
With more stuff blocking the front end it may be different. All I have is the spare tire with a mesh cover (on a Draw Tite bracket that mounts it out from the grille a ways), and in my experiments way back when that did not affect things much or at all vs. nothing in front. My experiment was a specific huge hill run in hot weather with no spare, a bare spare, and the spare with the factory Continental cover on it (solid disc). I didn't like the look of the Continental cover on the front so I went with one made from a Phifertex type material. I prefer the look and it does breathe (bugs brush right off, which I also like).
The ultimate authority for me is the Scan Gauge II's temp readings. As long as I'm seeing FWT below 200º and transmission at 185º or below, I'm a happy camper.
BTW, if you install one of these transmission coolers, a tip is to paint the front black before you install it (I used high temp spray paint). Otherwise your Ford will look like it is wearing braces on its teeth.
Here are some photos:
1) Original trans cooler (in front of radiator)
2) New trans cooler in same spot (before painting black so it's easier to see)
3) New cooler box showing model data