Shane Williams

For all the extra money you would have to spend to install a trans
cooler, etc why not just rent a larger U-Haul truck capable of
carrying all your goods including the caddy. Or maybe just tow the
caddy behind the truck just like the RV owners do.

Either way, you should probably price out the most feasable solution,
and the one you are most comfortable with.

Also, while the trailer DOES have brakes of its own you should still
be concerned about the added momentum that the trailer will provide as
you pull it behind you.