Toyota should get a round of applause for the Trail Edition. If you require a locking rear differential or have so much gear to carry that you need a real roof rack, you'll want to be in the 4Runner. The rest of the time you'll want to be in the Grand Cherokee. If you had both in your garage, you'd drive the Grand Cherokee most of the time and pull out the Trail Edition on weekends.
Our suspicion is that, among $40,000-plus SUVs, most people would rather have a more versatile coach that they can enjoy driving every day, knowing that, if there's a camping vacation in the future, they can still pull it off. If we're talking about versatility, and a choice between these two, it's the Jeep that comes out on top.
First Place: Jeep Grand Cherokee Limited
Great daily driver, with an elegant cabin and easy-to-use four-wheel drive. Short of crossing obstacles where you'd need a locking rear diff, it will take you just about anywhere.
Second Place: Toyota 4Runner Trail Edition
Fantastic off-road, but old-school -- it's too specialized to be as much fun day to day. A Limited brings more lux, but you can't get all the 4WD gizmos.