The triple tow issue is a bit complex I fear.? Let me bring up a few points.
1.? Tow vehicles have a specific tow rating which should never? be exceeded.? ?That tow rating includes all the trailers hauled.? You haul a jeep, you add some 4000 lbs to the payload of your 5th wheel.? Now if your tow rating exceeds the GVWR of the 5er plus the 4000 lbs of jeep and by a comfortable margin fine.? (For Colorado that margin should be 20%.)? However if it does not you are compromising your truck, your saftey, and the safety of every one riding with you and near you.? ?Frankly, most of the folks buying 5th wheels who come here for advice seem have a hard time find trailers that they can safely haul -- even without tacking 2 tons of payload on to the back of a loaded trailer.
2.? The laws of the states vary wildly on this subject and the tables are to put it as kindly as possible, inaccurate.? ?For example, California is shown on many as approving triple tows.? So fine, right?? Not really -- there are a few little bitty stipulations.? ?First of all, no passenger vehicle is permitted to triple tow.? ?A pickup is a passenger vehicle.? So that means you better be pulling with a medium duty truck.? ?And then there is the matter of a drivers licence.? To tow more than a single trailer, you must have a commercial Class A license with a special endorsement for multiple tows.? ?In short, not every big rig driver is licensed to tow more than one trailer.? No non-commercial license holder, A, B, or C, is permitted to.
Nevertheless, the bloody tables say that California permits multiple tows! They just leave out a few details.
Look, the sensible way to haul a jeep is with a motor home of the proper tow rating, not a trailer.