I towed my jeep with my 27 foot 5th wheel a few times years ago. Please note a few times , flat ground close to home stuff. let me say for a non professional driver you are rolling the dice . I had a lot of truck driving experience moving heavy equipment around like 9 axle low bed stuff in my younger days like Cranes, dozers and scrapers . I have a doubles indorsed commercial licence . (A must to haul doubles)
My 06 Rubicon ( highly modified) jeep weighs about 6,000 pounds , towing brakes installed about $500.00 .
Toy hauler modification to handle the tow hitch and weight of the jeep, about $ 1400.00 at the frame shop . $ 10.00 worth of aspirin from the stress and head aches
1. Do you have the licence to pull doubles in your state ?
2. Can your truck legally pull the combined weight, The big one, can you stop it ?
3. What your states max length on the first trailer , Calif is 28 foot
4. whats your states max overall length front of truck to rear of jeep. can you make it ?
I hope this gives you some food for thought !! Good luck
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