Re: Wrangler 2015 or Cherokee 2015?
If the Cherokee is too small then it will never work for you.
If creature comfort ride is paramount then seriously consider the Grand Cherokee. My wife's GC is great. I took it camping recently from South Florida to North Georgia... fast, powerful, comfortable, plenty of room. A V6 Cherokee has all that but it is noticeably smaller.
I own a 2008 JK 4 door. Ride wise it is light years beyond my old CJ.
It is my DD, beater, fun-in-the-sun, don't care if it gets scratched, stick shift, get out of my way because if you don't I'll just have to hop the curb... vehicle. I have driven it all over the SE USA. The ONLY thing I wish it had was the 3.6 pentastar engine that the 2012 and later models have because that motor helps a lot when traveling.
I have a hard top and soft top. I don't have issues with South Florida thunderstorms but it is loud when it is pouring.
Car prices new? There is no comparison. If I had $35 - $40k I'd buy a GC. Much more bang for the buck. JKs are cool but they are over priced because of the demand.