Im not a terribly big fan of the subaru 4spd auto.. i mean, its fairly reliable, but stupid things do occasionally fail on it, like a pump shaft as thick as your pinkie that doesnt cause any real damage when it fails but leaves you dead in the road.
Im more for the range rover than the outback because of its greater utility value and funky-cool styling. And a modicum of torque.
My previous utility vehicle was a 91 Cherokee. I towed with it, semi-frequently, but built it for towing. I made custom leaf packs with 3/4 ton Dodge van springs, Bilstein shocks, and my Limited model came with a rear sway bar. I had 16" Grand Cherokee wheels with good LT rated tires, Hawk HPS pads, and a bigass transmission cooler. They are underbraked for themselves, so trailer brakes for any decent load is a MUST. The 91+ 4.0 HO is such a great motor though.
I agree about the brakes.. Also, i went from 265/75r15s to 225/60r16s on one of mine and it completely changed the feel of the thing for the better. But, to many people smaller tires on a jeep doesnt make any sense, and if you NEED 4wd i can see why some might feel that way. Still, keeping a large overall diameter but a smaller,stiffer sidewall on a larger rim is bound to make a drastic improvement on a cherokee. Luckily the cherokee has the extremely common 5x114.3 pattern so its super easy to find wheels for. Id get some of those 15x8 or 16x8 diamond steelies for ~$50 a piece with different backspace so they move outboard a bit.. Wider track, wider rim, less sidewall deflection, all would help a cherokee.