I think we've all managed to drop the pin in the sand, or onto a hard surface where it bounces off into another dimension  
 
 I'm not sure how best to explain it, but since the halyard pulley is higher than the forestay hound, I tie the halyard thru the shroud extender and shackle, so that the rope and knot are above the pin holes.  This points the shroud extender down a bit, and lines things up better for pinning.
The other thing to remember, the rig doesn't need to be very tight.  Not like a typical monohull.  So just pin it where it's easy to insert.  Folks who race Waves always keep the rig really loose and sloppy.  For recreational sailing, it gets a little noisy if you get into powerboat chop and the mast starts flopping around; but I'll just grab a shroud and pull it tight until the chop subsides.