To load the boat back on the trailer, I usually just back minimal trailer into the water,
(just enough that very little of the end of the boards are in the water and the wheels and axle are not in the water to have lilies pile up on them)
I then load the boat as far as it will go on the trailer, then I winch it the rest of the way onto the trailer.
What this does is not allow the lilies to be mashed/drug between the boat and boards.