I always installed mine in the output line of the tranny because I wanted to see what the working temp of the tranny was - I felt this was a truer picture of what was going on - just my opinion. I thought this was good because coming from an industrial background when we look at cooling systems or hydraulic systems temps we always took the temp readings from key points in the systems or the output line before any cooling took place, reason was we didn't really care what the reservouir temp was which the pan on a tranny is a reservouir. I know from doing some reading that the port that Joe is talking about pretty much gives the same readings as what the pan does - is it wrong - no you just have to adjust your temp ranges vs mine.
I know with mine you can run 225 degrees all day long and not have a problem, if you get over about 260 I would slow down and let her cool a bit. now word of caution don't shut the truck off to let it cool - just place her in park and let her circulate the fluid through the coolers so that you can dump the heat if you shut her off she will just sit and heat soak the fluid, which can lead to overheating spots - not good....
Now to protect the coolers and the tranny I would place an external tranny filter BEFORE any cooling happens this way you will trap the debris before it gets to the coolers (hopefully) if and when the trans dies (as you suspect/plan) then back flush the coolers before reinstalling them. If you don't add the extra cooling you will surely kill it pretty quick with doing plowing and you will seal it's fate pretty quick. You can pick up a Perma-Cool trans filter from Summit Racing, Jegs or just about any high performance dealer of autoparts.
Part number PRM-10678 cost 40 bucks. Uses a standard oil spin on oil filter (it's the one that just about every Ford Gasser takes FL1A or something to that effect).