Just trying to clarify, is it happening only when it got cold? And do you have the factory belt driven fan on it? I see you're in Missouri, not sure how much Bio Diesel they run by you, but that can be a problem. In Minnesota, they specifically regulate it to a low content in the winter months due to gelling concerns. Two things possibly causing your problems, not a definite:
1: Factory fan moves a lot of air, which is good, unless you're trying to build heat. Especially if you're on 5.38 gears. And these little engine don't build a ton of heat. So the excessive air can cool the Diesel down to a gelling point if is cold enough, AND you're high in BIO-Diesel content.
2: Too high Bio Diesel Content for the temperature.
Howes and 911 Diesel Treatment don't really help the Bio DIesel as much as they do for Ol' Dino DIesel. If Bio Diesel is your problem, what's happening is, the cold air is gelling the fuel before the pump. I.E in the filter and lines to the high pressure pump. The in-tank pump is strictly a low pressure feed pump. It won't push gelled Bio. If the Bio-Fuel turns to "Bacon Grease", which is what actually happens above 10-15% bio in the real cold, no feed pump will push it through and the pressure pump will starve, and then....chug out and die.
I've been selling HD Semi Trucks for years, believe me, I've seen this in person many more times than I would like. Not saying this is what's happening in your case, but it sure sounds familiar to me with what you're describing.
If there was a way for you to pull that fuel filter AS SOON as it gave you the problem, not allowing it to warm up at all, you might catch the problem. It would be black, sticky looking grease. But the problem is as soon as you leave it sit, without the engine fan blowing around, it'll probably loosen up and look fine. Within minutes actually. Which would explain why you say it starts up fine again.
You could also remove the fan blade as a test, since it's cold, and drive it in the same conditions. It definitely won't overheat if you're moving, but keep an eye just in case. If the fan was the problem, it won't chug out on ya. Then you found the issue. If that ends up being the case, then electric fans would be the remedy.
Sorry for long thread, but this isn't a cut and dry issue. LOL
Hope that helps!