Reminds me of a trip to Michigan from Virginia a few years back for the annual Model T Ford Club week-long tour. I towed a 29 foot TT behind a 30 foot rollback truck, which was also hauling our 1923 Ford Model T. Worked very nicely, but don't think I'd try it with a boat.
2003 Ford F-350 V-10 Crew Cab 4WD Long Bed
2004 Jayco Designer Medallion 29 RLTS 5th wheel
Bill, Gayle, and Mindi (dachshund)
Retired at last !
Nothing is foolproof to a sufficiently talented fool.