This is definitely a question I pondered with myself before I went with the Trailhawk. Since I live in Wisconsin, we don't really have many off-road trails, if at all that I can recall off hand (anyone from the area care to chime in?). What we do have though are usually some pretty harsh winters. Now, you might suggest that if I was looking for a winter beater, then why didn't I just go for a non-TH trim, or even a Cherokee XJ? Well, I was thinking ahead. I was thinking of all the things that I plan on accomplishing within the next 5-10 years, including towing, off-roading (nothing too hardcore), hauling, etc, all while having the creature comforts to make the journey getting there and back to be relaxing. I also use my TH for work purposes as well as a DD, so hauling concrete cylinders, testing equipment, and other doo dads are not an issue. And given how a lot of the terrain I might encounter would be where no roads exist, I wanted the extra ruggedness.
Again though, you might still say why I don't then get something older such as the Cherokee XJ because it'll do all of those things (minus the creature comforts part, and gas mileage). Well, it's precisely the creature comforts why I was sold. Cold Weather package, panoramic sunroof, navigation, remote start, bluetooth, leather seats, etc. I believe there is a definite draw to owning a vehicle you can drive on pretty much any sort of terrain, and then drive it back home with your friends or family at the end of the day. This is something I know a lot of pick-up trucks are becoming, but I am not a pick-up person (Although I do like the new Honda Ridgeline). Before the TH, I had considered the Ford Escape, Nissan XTerra, Toyota FJ Cruiser, Toyota RAV4, Toyota 4Runner, Chevy Equinox/GMC Terrain, Honda Pilot, Jeep Wrangler, Honda Crosstour, and a couple others. In my opinion, the Cherokee Trailhawk was the best compromise for what I wanted, and how I was going to drive it every day.
We'll see how my decision faired though in a couple or few years.