Fed Highway Regs will drive this with some modification by state law. A doubles commercial configuration would be limited to a max of 75 feet overall, with each trailer being no longer than 28 feet on Federal Interstate Highways. State and county roads are more likely more restrictive depending on location. This configuration would require a CDL to drive legally. A 40 foot fifth wheel pulling a Jeep most likely would exceed 75 feet overall length and the 40 foot fifth wheel exceeds the 28 foot limitation. You might be able to do this legally with an over length permit for each state visited but that will be expensive and a major hassle. Without a CDL you are going to have trouble. Max length for an RV configuration on Interstate Highways is 65 feet overall length, not 75 feet.
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