Heaviest I pull is a 6x10 enclosed v-nose trailer, weighing around 2500-2700lbs when fully loaded. I also have a Vanco Big Brake kit (dual piston 48mm calipers + Black Magic Brake pads), 10" drum brakes on the trailer and a trailer brake controller in the Jeep. I have heavy rate rear springs with AirLift load leveling airbags to help control the weight & tendency to bottom out. I've got a heavy duty rear bumper with integrated hitch, and frame tie-ins. Trailer also has a friction sway control bar if necessary, but so far trailer sway hasn't been an issue.
So stopping & controlling the trailer is handled...but now the problem has become maintaining speed. Big loss of power & heating up the engine/trans when climbing mountains & hills. Even with 4.88 gears & a 1-ton trans cooler...
....so I'm currently searching for a used 3/4 ton diesel, which will climb those mountain passes without straining one bit.