Towing your Jeep often entails a steep learning curve. It's not until you've lived through near-death experiences or multi-thousand-dollar repairs that you realize you need more tow rig to move whatever it is that you are towing. I've towed my Jeeps with just about every kind of owned, borrowed, begged, or stolen vehicle under the sun. Like many people, I've always tried to get by with less than I needed because I didn't need a tow rig all that often. I certainly couldn't justify an expensive 3/4- or 1-ton diesel truck to tow only a few times a year.
My first tow rig was the least likely of all of them and perhaps the most dangerous. It was fine as a daily driver, but as a tow rig my '90 four-cylinder Toyota shortbed pickup was pathetically underpowered, underbraked, and triggered a white-knuckle driving experience when pulling a Jeep. The truck weighed about 2,500 pounds and I used it to flat-tow a 3,500-pound Jeep. Needless to say, the rear end of the pickup would push around mountain corners (especially in the rain) unless I really loaded down the bed with camping gear and firewood.
However, adding the extra weight chewed into the already limited hill-climbing horsepower of the 2.4L and four-speed manual tranny. The truck was rated to tow something in the neighborhood of 5,000 pounds, but certainly not safely and not in my configuration. Eventually some lug nut pulled out in front of me on a rural road, I slammed on the brakes, my towbar broke loose, and my Jeep slammed into the back end of my truck. It was a bummer, but at least I didn't die. Rear ending yourself makes for an interesting insurance claim.
My next tow rig needed to be a fullsize truck with some weight and a V-8. I gave up on flat-towing and purchased a trailer. I bought a '79 F-150 prerunner desert truck complete with Chevy drivetrain. As a tow rig it wasn't perfect, but it was at least safer than my Toyota truck, plus it really hauled ass through the whoops in the desert. I later realized this was not a good attribute for a tow rig due to the fact that the soft rear suspension collapsed whenever I hitched up a trailer. On one of my first towing trips, I smelled smoke while climbing a particularly steep grade.
I pulled over to take a look and found that the TH350 automatic tranny was getting so hot that the urethane transmission mount was melting. So, doing what any dumb 20-something kid would do, I let it cool off a little and continued on out to the desert over the mountains. Everything was fine until I was ready to leave at the end of the weekend. The transmission in the F-150 slipped badly in Reverse, First was the only forward gear that worked, and I was 150 miles from home. After replacing the tranny in the F-150, adding a large tranny cooler, and installing a fresh engine, I figured I could tow anywhere. Boy was I wrong.
While pulling up a steep desert grade in the summer I noticed the engine and tranny temp rising close to the red. By the time I got home I had wasted both my new tranny and engine. I finally gave up on the old F-150. For several years and until I could afford one of my own, I rented diesel box trucks when I needed a tow rig. I eventually ended up with a new '04 Dodge Ram 1500 Quad Cab. I optioned in the Hemi V-8 and 3.91 axle gears to achieve the maximum 1/2-ton tow rating (at the time) of 8,600 pounds. In most cases, my Dodge has been more than enough truck for me.
This year on the annual trip to Easter Jeep Safari in Moab, Utah, I had the chance to tow with the king of light-duty tow rigs, the Ram 3500 Crew Cab dually Cummins 4x4. It's really way too much truck for my 5,000-7,000-pound loads. But it was more stable than anything I've ever towed with. It pulled like a freight train easily maintaining 70 mph speed limits up the steepest grades. It stopped and handled as if there wasn't even a trailer attached. Looking back, the Ram 3500 made towing a much less stressful experience than towing with my Toyota, a number of twitchy motorhomes, worn out box trucks, or a clapped out F-150- all of which no doubt gave me much of the grey hair I have today.