If only the new Jeep GC SRT8 had more than a 5k tow rating, I'd definitely consider it. My trailer loaded with car is more than that. 5400 to be exact, so I wouldn't want to take any chances should I ever wreck while towing and my insurance carrier questions if I was towing within my equipment's rated capacities.
Cayennes are nice inside but I just can't get over the looks outside. Plus, I didn't want to be one of "those guys" towing a Porsche with a Porsche. Also, Cayennes are just too expensive (I'd want the Turbo) to use and abuse with towing duties. I'd feel bad beating it up like that, less so with its sibling, the Touareg for obvious reasons. Raptor is a truck that's meant for hard work and getting dirty, and I guess that's what appealed to me for a tow vehicle/daily driver.
I'm glad you posted this thread because I had been having the exact same thoughts. I fell in love with the Raptor and was trying to convince myself that it was the perfect vehicle to replace my Cayenne Turbo S which also happens to be what tows my 996TT to the track (yes, I'm the guy that tows a Porsche with Porsche but keep reading and everyone will be happy
). I love the Cayenne and it is a beast when towing, probably just as good as your Touareg, but I was just itching for something I could take and beat off road while also being able to tow my track car. I happen to live in a city as well and one that may arguably be worse than Chicago...San Francisco. Like you, I never drive my 911 around because I can't get anywhere without being extremely cautious (I'm a touch lower than GT2 height).
Well, long story short, I some how rationalized with myself that a Raptor made sense (which I will be honest, it doesn't!) and went and ordered a 2012 last weekend!!
The wait is going to kill me and I'm sure as much as I'll hate taking it around the city, I'll love it at the same time! You should go order one so I don't feel like the only idiot who lives in a city and bought a Raptor.
I used to own a Jeep SRT8 before the Cayenne but it didn't even come with a hitch and took a decent amount of work to get it in shape to tow 5K+ lbs so I scrapped that idea. The SRT8 was a blast but wasn't the best in the snow (Tahoe) although I'd bet she'd be alright with a decent set of snow tires aside from the fact the front valance was literally 4" off the ground...almost as bad as the 911. Well to be fair I did have to get chains to get to my house up there one weekend and she looked pretty badass if I don't say. And as much as I love the new SRT8, I'd still say go for the Raptor!