: My crazy idea is to hitch the boat trailer to the camper. That got
: about 1 second of serious consideration.

Depending on the kind of popup- the roof may or may not be able to handle the weight. It's one of those things, many people have done it, some have never had issues - other have had nothing but problems. I have a Coleman pop-up with a roof in the middle of the years that were problematic for Coleman. I won't even consider putting the kayaks on top.

Same with adding a hitch to the back of the pop-up. People have done it - some claim no issues, some claim many issues and many more claim it's a bad idea due to decreasing the hitch weight on the vehicle.

The kayaks go on top of the truck - no the question is how. I have a friend who has racks on top of her Tacoma without issue. She has a little fold-up step stool that she normally avoids using (in lieu of just stepping up on the tires and the door w/ it open). The ladder rack is probably the simplest idea. Thule/Yakima racks on the cab are another.

I'm having the same conundrum - only I'm looking at BIG trucks and a fifth wheel (so I won't have a truck bed).