Well, that Trailhawk looks lifted, has rock sliders, bigger KO2s, and starts at $10K more than the CrossTrek. And if you want a bit of a laugh/cringe, here's a stock-looking CrossTrek (non-stock wheels but shitty-looking tires) on Hell's Revenge in Moab. He was very sloppy and destroys the front bumper and probably puts some good dents in the undertray, looks like he's having fun though. But with clearance-oriented bumper, 2" lift, better wheels and bigger tires, and rock rails, it would do just fine and still cost $5-10K less than that Trailhawk.
The Trailhawk will still be better on the harder off-road stuff, with the low range and locker.
But the stuff you want to try solo, 25 miles from a main road, out of cell coverage, in your daily driver with no winch, is just not going to be that much different between the CrossTrek and the Cherokee. Bump a rock wrong and bend/break a tie rod on either vehicle and you're going for a really long walk. High-center on a big rock? Going for a long walk. Come to a steep slippery down-hill you might not make it back up? Probably time to turn around, or you might be going for a really long walk. The off-road recovery cost will be bad but starting a 10-mile walk 1 hour before dark will be worse.
And both Hells Revenge and that Wheeler Lake trail look like trails you should probably do in a group, or at least with a buddy, unless you're in a dedicated off-road rig.