It is true that fuel distributors pretty much take care of the cold weather performance issues, but there are still cold weather issues if you don't pay attention, for example, driving north with a tank full of southern fuel, or if you buy fuel from some lonely station that maybe orders fuel once a year. In either case, a shot of Power Service anti-gel might be in order, "just in case," and "it can't hoit nuthin'."
It must also be noted that you can size an engine too small for the job at hand regardless of whether it is gas or diesel. The acid test is to drive it up a steep mountain and see what it does. It is true that diesel engines have a higher thermal efficiency, meaning in practical terms that they will burn less fuel to drag a pound of "stuff" any given distance, but this too is a function of the specific engine sizes involved.
There are a couple things folks used to driving gassers need to know when they find themselves behind the wheel of a diesel. First is that diesels do not react well to being run out of fuel. In the old days, that used to destroy the fuel pump and injectors, which not so much any more, but it is still hard on them, and getting one that has been run dry restarted is a HUGE pain in the butt, wise grasshoppers take care to never do that. A second thing is that you have to retrain yourself to pay attention to putting DIESEL fuel in the tank and not refueling while on autopilot, which has been known to get you a tank full of gasoline. THAT is a very expensive mistake to make, btw.
As for your question about the 2014 rig with the 340 HP Cummins, I refer you to the acid test above.