Hi Dan,
So tell me about your A Cat.
I am with you. Even the best tent is still at ground level.
I have thought about carrying a cat on a pop-p also.
I spoke to the guy a Spring Fever who carries his 18 square on his pop-up.
He told me some very interesting things about pop-ups.
Most of them are built on a very lightweight frame and springs such that they can't carry much additional weight. He had found a large one with so much additional capacity that it had a large external storage box.
Most of them have very lightweight tops that can't carry much weight either so you may need external supports for the boat.
Remember that a soft pop-up still has canvas sides that can leak like a tent.
I have been trying to find one of the hard-side pop-ups and put it on a bigger, stronger frame with supports for the boat.

Good luck.
Sam

P.S. I bet the Camp Hatteras Regatta had alot of people looking for better tents.