Willie, you could try tying the bowlines so that the tail is on the outside and the smoother part of the knot passes over the shroud.
I've also seen some people use PVC pipe on the foward shroud as a roller.
What I did is use one single long line with a simple knot at the grommet. Loop the line in the middle. Push the loop through the grommet. Pull the ends of the line through the loop. That's it. Works well.
Mike, what name are you going to give the sail? Maybe "The Whomper"