^ Great idea! I have seen similar here.
I'm going to guess why that isn't as popular in the US is that the same type of cab/truck/semi/tractor is used for every type of trailer here. Once you make a specialized rig, it cuts into profits as it will only haul cars (or whatever the tractor was designed to haul) when they need to be hauled and limits the driver to just hauling that specific type of load.
I've seen longer tractors and shorter trailers here, but not many. I've seen them used for shows (car, music, etc) and they were usually covered/boxed. This would allow them to get in to/out of cities easier. Most cities/towns have better access here. Wider, straighter roads that are closer to hywys. There aren't many dealerships 'downtown' and if there are, the cars are probably driven individually from a drop off point so the rig doesn't have to drive on tight one way streets or blocking traffic to unload.
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As why the guy beached it? Can only guess. Probably took a short cut on his route, couldn't find a turn-around, or purposefully took that route for his own private reasons (visit someone, favorite food etc).
That specific route might even have weight/length limits and he broke them using that route.
Usually when we see this sort of thing like in the video, the driver is either inexperienced, in a hurry, lazy and cut corners literally, maybe lost but that isn't as common with modern GPS or under the influence or some other driver stupidity.
There's about 2.6 million miles (4 million km) of paved roads and not all of them are going to be safe for big rigs nor signed to direct or limit them. It will take the driver to make safe/smart decisions.