The Tregs are nice...very classy vehicle. And I really like the idea of the torque-monster V10 diesel in the TDI model. But I have a hard time recommending VWs to people...I've owned 3 different VWs of various years, and still lurk on a couple of VW boards. They're great-driving vehicles, but they're plauged with niggling issues that can drive you nuts, and VW dealer service is very inconsistent. The dealer that I bought one VW from had a great service department, but it was a combined VW/Infinity dealer, so the mindset in dealing with all their customers was to deal with them as if they had all bought a Q45 even if they had a base Golf. I moved to a different city and started going to the VW dealer there...lousy service experience....worst I've ever been treated at any dealership or service department.
My former Jetta was a great-driving vehicle that I loved. But it was very expensive to service, it was tough to find even simple things like oil filters anywhere but at the dealership, and had a couple of problems that plauged it the entire 70,000 miles that I drove it. It would periodically die for a second or two while driving down the road, then instantly re-start like nothing had ever happened. The ABS wouldn't work if the car ran for more than about 30 minutes...the dealer ended up replacing pretty much everything in the braking system and it still did it. And the seats used cheap plastic locator tabs in the seat tracks...after about 6 months they'd wear from just moving the seat back and forth once a week to vaccum the car, making the seat wobble (and no I'm not a grossly overweight person...6 ft and 215 pounds). Those three things were never completely fixed despite spending more time in the service department than any vehicle I've ever owned.
I can't really speak for Jeep reliability since my WK is my first Jeep. But other than brakes on the early WJ, most of the problems that people have (that I've read about anyway) seem to be more related to lots of miles and lots of hard off-road use than any sort of real design flaws.