Judge Dredd easily fit in a 2015 Jeep Grand Cherokee Limited. It's a tight fit at the hatch (see close-up photo), so you have to load it as close to the center as possible. Once the head clears the hatch, you can slide it over to maximize cargo space (if you need it).

It was pretty easy loading / unloading it.

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I figured some people would want to know these things, so I did check it out a bit. There was really no information on the 2014+ models, so I figured I would note what I could.

See attached photo. It wasn't sitting against the lift gate, so it could have been moved back a little bit more. I had the legs wrapped in the blanket against the lift gate. It could have been pushed toward the driver's side 9 more inches (I measured it before unloading it).

The driver's seat was not adjusted and was on my memory setting. I am 6'0 and normally have car seats in the back and never have issues with leg room.

It MIGHT be possible if you folded both seats down, pushed it forward, then slid it as far left as it can go. I THINK the Grand Cherokee was exactly 32 inches from the door to the right rear passenger seat, minus however far the wheel well sticks out (I think it's about 6"). It's another five inches over to the head rest, so as long as pin / head clears the height of the rear seat, it should have plenty of width. JD is a superpin, so if it will fit, most should.

I just measured the rear seat height and the height of Judge Dredd at the point where the head folds down at the lowest point (towards the coin door). I can say with some degree of certainty that it will NOT fit IF you load it coin door first; however, if you load it head first, it MIGHT fit. The rear seat is about a half-inch taller than JD at the lowest point of the head (see photos), but if you load the machine head first, it MIGHT be enough to clear the seat and not hit. I can't guarantee it, but it looks POSSIBLE. The head is 10" long and would go from being about 24" to 21" to the bottom of the head if you load it head first. The Grand Cherokee rear seat is only about 5" deep. I think if you did it this way, you probably could have a passenger in the right rear; just don't put someone who is claustrophobic there.

TL:DR

The Grand Cherokee has plenty of room for a 6'0 person to haul one widebody WPC pin without adjusting the driver's seat. It's probably not possible to have a rear passenger if you load it coin door first. It looks very possible to have a rear passenger if you load it head first, but that person will probably hate you.

No idea about the regular Cherokee; make sure it has 30 inches of height at most points in the rear lift gate and that both seats fold down.

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Keep her away from the Grand Cherokee if you want to keep your Durango. Having said that, they are basically the same car. Steer clear of the diesel; I have heard nothing but horror stories from the people I know that owned them.

The 4Runner is good also, but it lacks a lot of convenience options like remote start, power lift gate (best thing ever), etc. If you don't care about any of that stuff, consider one of those. It's an actual truck, though, so the ride isn't as good as the Durango or Jeep. Resale value is among the best of any vehicle. And most importantly, it easily hauls pins.