Tom,
Looks to me that the trailer would not be long enough to haul both at one time. Also i believe the center is open. I have an open center car hauler i used and i ended up filling the center cause the tractor tires only rode halfway on the trailer. (disaster waiting to happen) also if the Z71 is just a half ton that amount of weight ( cub, SA and trailer) would be quite a load and make for a long trip but can be done. But I would not recommend it. My days of a half ton are over. I am tired of hauling too much weight for the truck.
I think you need to either find a different trailer or rent a utility trailer and make two trips. I think that would be safer.
Just my .02
MJ