Well...I ended up going back to my cab cover invention so a rigid ducktail is definitely out of the mix. Trying a soft ducktail instead made out of some left over Tyvek from my cab cover. Taping it along the leading edge with some Tyvek tape to the cab and using some sort of stiff material on the trailing edge will allow me to tuck the ducktail under the cab cover when it's in use. The ducktail's trailing edge will be secured to the aero cap when the cab cover is not in use. This will keep the rain/airflow from entering the gap between the cab and the aero cap. The soft ducktail will move with the flexing of the frame/bed and shouldn't stress under the load. I'll try some velcro ties to tie the trailing edge down. I don't know if it will try to balloon like a convertible top or not. Guess I'll have to find out and see.
Currently out in Nebraska and there is some rain expected tomorrow along with a big drop in temps. We'll see how well this will perform.