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 SSQ5, Prestige
2007 Audi RS4