It is a matter of a person's sense of esthetics. A farmer does not care about a cow being ugly or not but how much milk he can squeeze from her tits.
First thought was curb sniffer. It better have one heck of a tight turning radius to justify that far of a setback.
The truck that was brought by for us to look at last week, talking to the salesman there are new X-Guards already available for it that are dealer installed options that protect the grill and lights, the one they are bringing us this week may have one installed.
The 440 we looked at recently was a midrise, had 6 or 8 cubby holes/spaces about the drivers head for storage, it was supposed to have cabinets in the sleeper but was shipped without them.
That truck would be lucky to make it more than 30 feet into our yard before the front bumper gets smacked up. Best keep it as far away from gravel as possible.
Have you considered getting a grader/dozer in to level out the 2ft deep potholes? The bumper looks higher than lots of the freightliners I've seen with the rubber skirt. Honestly I'd love to have a truck with the kind of dinette setup these trucks have. A place to sit down besides the bed or the seat I work from all day long.
My boss and I had that same discussion, but one thing we noticed is they come with lopro 22.5, 11R's are an option.