just chiming in 
hey all, I owned a 2009 loaded laredo for a couple of years, and now in the market for another.
Thought I would add some of my ups and downs, since this is a post about the usefulness of the WK.
We bought ours as a CPO with something like 35k miles, clean looking.
Had to replace all four wheel bearings within two weeks of buying it.
Would smoke out the tailpipes at really odd times and no dealer could replicate. A year in and it finally died on the GF while she was on the road in IA, dealer in waterloo diagnosed it as a plugged PCV valve in about 30 minutes. (several other dealers did nothing because nothing came up on the computer...typical)
It developed a weird buzz/vibration and again 2 dealers told us to ****** off before a really awesome dealer in the tiny burg of Louisburg, WI
(http://www.louisburggarage.net/) diagnosed it as a transfer case on the way out. $500 deductible later and it was replaced no questions asked.
So those were the definite low points. (oh and that one time I got a flat in Waterloo while it was about -30F in January)
I honestly think I bought a lemon that was rode hard and put away wet. because aside from the above problems I never had anything significant happen. We sold it with about 55k miles and we have regretted that ever since.
Our Laredo was loaded: uConnect stereo, backup camera, remote start, heated seats, leather, sunroof, tow hitch, etc. It also had the limited run dual plug 4.7L V8.
Do not confuse this engine with the older Chrysler 4.7 V8!!
While the dual-plug head definitely points at some engineering mistakes the results form this engine are awesome. We got as high as 25mpg on the highway (albeit with a tailwind) and still when you put your foot in it the power just poured out like velvet hammers. granted you dont get 20+mpg when you are spitting out 300HP but having the technology to do both, in my opinion, as amazing. I previously owned an XJ and an MJ and the WK is hands down better to me. Driving to the trailhead is actually bearable and downright comfortable!
I had the QT1 system (only 4wd HI and LO) and even on the not-so-great stock Frontera tires we still drove that Jeep all over. I drove up the Dickeyville hillclimb, okay so it was the backside but its freakin steep and not maintained!
Sadly I do not have any pictures on this computer to share.
My closing thought would be:
When me and the GF went out to Colorado two summers ago one of the things we agreed on was that our WK would have been way better for the trip than our Silverado.
