Raking Rudders Correcting Helm on a Hobie 16 by Bill Mattson in Volume 2 issue 7 of
On The Wire shows how to fill in and re-drill the holes in a rudder.
I have followed his method on several Lexan rudders and used JB Weld to fill in the holes while the rudders were flat with a piece of masking tape on the bottom. I do not have a drill press but have used a piece off of one of my broken rudders with a hole already drilled (for maximum rake) in it that I clamped to the rudder, so it would act as a guide for the drill bit of my hand held electric drill.
http://www.catsail.com/archives/v2-i7/feature3.htm