I've only pulled a fiberglass boat (have no idea what a '66 Chrysler boat .. yes, Chrysler boat weighs) and my '77 Jeep CJ5. The boat was heavy on the old saggy suspension but, it pulled pretty effortless. The Heep has zero tongue weight as the front wheels support the vehicles weight. However, it is noticeably heavier than the boat was on acceleration and braking.
Curious, how much more power does the VG33E have over the VG30E? Would it really make that much difference when it comes to pulling a trailer?