I've got a 2014 Overland with the Hemi, off road II, advanced tech group, etc.
I've actually been pleasantly surprised with the Hemi's mileage. I burn midgrade and sometimes sorta "pass in a hurry" but at about 3600 miles am running in the 17-18 range, where thats a lot of commute and a lot more mountain driving in sport mode.
Using the instant mpg display, once you are more or less level driving, I honestly don't see a difference in sport vs eco mode and the aero mode makes it drive almost like a sports sedan. The sport mode does suck more gas on uphills in particular, but for two lane mountain road passing, it does get rid of the "hold on bubba, I'm taking a break" syndrome of the eco mode when you stomp on it.
I don't think you can get the Hemi with anything but the top level 4wd and electronic LSD. I wouldn't recommend it if you plan to stomp on it on wet roads with those godawful Michelin Latitudes unless you like wheel spin.
The 8 speed may have a lot to do with the ability to squeal tires and yet not take out a loan for a tank of gas.