We have both the overland summit and srt8. The overland is a really nice car, very luxurious with some great features. It just doesn't compare in terms of handling and performance to the srt8. However, the price differential between the 2 is more than a lot of people can understand. If you've got the extra coin, go for the srt8.
We bought the overland about a year ago after looking at bmw x3 and acura mdx. I purchased a wk1 srt8 thinking I would be happy, after passing on the initial phase of ordering the srt8 last June. I traded it in after putting about 1200 miles on it, the wk2 is what I should have done to begin with. I had enough experience with the overland and should have realized the wk1 wouldn't be enough.
2014 Jeep SRT
2013 Audi TTRS, Exclusive Pkg
2014 Audi SQ5, Prestige
2015 Ram 1500 Limited 4x4