Trans temp is monitored by the TCM and there's a light for over-temp in the annunciator panel.
The data is also on the CANBUS so if you install something like the Bluefire dongle, etc you can display trans temp on a tablet or phone.
These trucks have pretty good transmission cooling and huge radiators with a ton of coolant (~12 gallons - which is the usual system capacity for twice as much engine [C15]). It's difficult to overheat them under normal conditions. I would monitor it a bit on the bus and then decide if there's even a reason to install a gauge - depending on your use case of course. If you are HEAVY towing through the desert it might be a good data point. For the majority of us that run ~25k lbs or less GVW you are unlikely to ever tax the cooling system. If your planning to tow with a 1088/89 then sure - what the hell.
I used to want all kinds of gauges but the reality is that in the vast majority of cases they are just sensory overload and not particularly useful. If the trans is overheating then chances are the engine coolant played a role, the engine is also overheating, or the transmission is spanked internally and slipping so it's overheating the fluid.... in which case it's not long before it needs a rebuild anyway so overheating is likely a short term problem to be followed by a period of not overheating because it no longer drives.
If you're determined to do it, I would weld a bung into the one end of the cooler near the hose ports, etc. Or find/make a fitting to install the sending unit inline with the trans fluid to cooler hoses.