jakemeister,
Regarding your questions about gelling, if he wants to be safe, then he should use an additive. The stations sell blended fuel which should be fine but there are mistakes from time to time which leave people with gelled trucks. Personally, I run the white bottle of powerservice in the winter. The red bottle which says 911 on it is specifically for dealing with a vehicle that has already gelled up. Once the fuel starts waxing, the reason that the truck refuses to run is that the wax crystals plug the fuel filter and prevent fuel from flowing to the engine. Therefore, to ungel a truck, you need to put 911 directly into the fuel filter and the fuel tank. A fuel air seperator won't help(there shouldn't be air to start with).
As far as an oil pan heater goes, if he is going someplace super cold(regularly below -30F), he could buy one of the pad heaters but otherwise, it isn't really necessary if you run synthetics. Since synthetics flow much more easily in the cold, they not only make the engine crank over faster, but they keep it lubricated better until it is up to temp.
There have been several comments in this post regarding duramax and 6. 5 engines not being any good in the cold which is not true. The 6. 5 wasn't great at cold starting but when I used to have one, I got it to cold start at -25F a few times without being plugged in which is quite respectable. A lot of people run duramaxs in the northern states and they seem to do quite well. The cummins does exceptionally well at cold starting but I wouldn't say that it does any better of a job than the duramax.