Re: 2014 jeep overland
The Summit gives you a slightly nicer interior with "suede like headliner", Harmon Kardon sound system, the advanced technology package, adaptive headlights with washers, unique polished 20" wheels and the unique body package, along with the Quadra-Drive II electronic locking rear diff - pretty much every available option. It is NOT available with the off road packages, but I am sure you could add the shields and probably the tow hooks as well if that matters to you. I would have considered the Summit, but my wife had to have the light colored interior with light carpet, and that meant Overland.
As for the SRT, it is a considerable increase over the Overland or Summit, and to me I would rather have a sports car than a 5200lb sports SUV. Most of the options on the SRT are standard on the Summit. I can get a used Cayman to play with in the canyons for price difference over an Overland or Summit; and I may just be doing that. If I could have just one vehicle, the SRT would be pretty cool. YMMV.