There is no way on earth I would tow my Boston Whaler CC behind my TJ. Too much boat, not enough vehicle. It would be irresponsible to other people who I share the road with and downright dangerous.
I am pretty sure that any Jeep Wrangler of any vintage qualifies among the handful of most ill advised and horrid tow vehicles and may well rate number 1 worst, especially if it is lifted and shod with big tires and wheels.
2006 TJ Rubicon, Custom 4 inch lift with Currie Arms, TF springs, RS9000 shocks, TF High Steer Kit, TF ST Dual rate anti-rock, TF front track bar, Yellow Box speedo correction, Black Rock 15X10 Streetlock wheels with BFG AT 33X15X12.5 tires, Line-X tub, Bed Rug carpet, Tom Woods shaft, Spidershade, Savvy corner and rocker armor, Exogate.