A Truck with a Different Look...

Well, you could pull over length on a flatbed using that truck without an escort by letting just a little hang off the back and the rest hang off the front of the trailer.

There's plenty of room there, but I don't see a headache rack behind the cab.

 

Most tarp trailers have a front bulkhead as part of the design, so they aren't suitable for over length loads. If he pulls a regular flat without a bulkhead, then yes, he should have a headache rack on there for his own safety.

 

I had a dream I saw an Argosy on Google StreetView

 

Probably the biggest user of those argsys is for hauling cars. They usually have a bed on the truck itelf and then haul a shorter trailer as well. I am willing to bet he bought this truck used and that is what it was originally and they took the bed off of it.
The lack of a deck plate further inforces my certainty not to mention I think I see vertical rust marks just behind the fuel tank which would be where the bed was bolted to the frame. Not sure though. I can't see it well

 

i love cabovers!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!