I'm a Grand Cherokee fan (drive a 1994 ZJ 4.0) but keep in mind there's no "time proven design." Current WK Grands share little with the previous WJ, and the WJ had major changes from the ZJ. As with many Chrysler products a lot of them have problems with little stuff. HVAC controls, electronic systems, and a certain amount of transmission trouble depending on model. The WK is also much more tuned for on-road performance, so it's given up the solid front axle suspension the previous ones were known for. No classic AMC 4.0 or Chrysler 318/360 in the new ones, either.
In your position if you were going Jeep, I'd see about getting a late (03-04) WJ I6 (slow, maybe you'd want the 4.7 V8) Larado--the stuff they added for the Limited package is trash, and makes for expensive repairs like the heater blend doors. You can also get WJs pretty darn cheap for a 5-year-old V8 truck. But the WK has better on-road manners and it's a newer vehicle, while stil using a nice big solid rear axle.
However, in your pricerange unless you want an SFA suspension I'd see how new a 4Runner or Land Cruiser I could get. Good reliability, crazy resale value. I don't think you can go wrong with either of those. Sure beats Jeep for long-term maintenance.
Nissan X-Terra isn't bad, it's based on the old Pathfinder chassis before it went big and goofy. I personally am not a huge fan, though. Nissan's partnered with Renault.
Honda Pilots, Mitsubishi Endeavors, Toyota Highlanders, etc aren't SUVs. They're 4-wheel drive minivans based on car platforms. If I were getting an SUV I'd want something with truck underpinnings and a selectable transfer case. Otherwise get a 4wd car or wagon.
Subaru Forresters are car based, but it's a small vehicle that fits it well. They're unique in that size class, and I have a soft spot for them. Might be too small depending on what you're doing. Lots of CV joints in the drivetrain, too.
As far as I'm concerned Explorers and Jimmys are just other unremarkable SUVs.