I have 32" tires and haul a 3000 pound, 19' ski boat. (it has a 3.5L merc V6 in it)
The only trouble with fishtailing is when you have too much weight in the back of the trailer.
I have no trouble braking but i also put in ceramic brake pads. i believe the wangler is rated for 3K pounds, and 5k if you an LJ, right?
drive smart and your alright, also, a weight distribution hitch would go a long way in a vehicle with a short wheel base. (to add stability not capacity)
Oh i have been denied at uhaul, with the hardtop on too...
TJ is 2,000 pounds and LJ is 3,500 pounds.
04 TJ - 2 KC Daylighters, 35x12.5x15 MT/R Kevlar, 3" coils, Rear 4 link, 1.25" JKS BL, 1" JKS BMML, 33 Eng. Hi-Clearance Skid, 8.8 with LS, D30 EZ locker, OBA