Lot of good points:
- The CAN IT versus SHOULD IT.
- Cross sectional wind.
The transmission cooler is built in to radiator, but I think it is pretty effective on the V6, at least for the 2015/2016 models. Actually, can anyone confirm same on 2017? I asked the question a while back about transmission temps on the 2017 when towing, but never got any good responses.
Once you get the boat "home" to Wisconsin, are you:
1. Going to put it in the water and leave it? (doubt it in Wisconsin.)
2. Pull it out every winter and relaunch every spring?
3. Launch it on a boat ramp or using a crane?
4. Tow it every weekend from home to lake, 10 miles? 50 miles? 150 miles?
If you are going to be launching it off a ramp, towing it every week a fair distance, etc., I would get a bigger truck. If you are just transporting it from Vegas to Wisconsin, I would rent a truck, probably even something heavier duty than that 1/2 ton Silverado that U-Haul offers.
The truck should have a transmission cooler. Also another thing, you don't want to "break in" your truck on the highway. So a 2000 mile trip is not the way to go.