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You might take a look at an old 'On the Wire' article that describes the drilling process, if you have to go that way.
http://www.thebeachcats.com/OnTheWire/www.catsail.com/archives/v2-i7/feature3.htm

As the article suggests, I would very much recommend a drill press if have access to one. If the drill bit 'wanders' or grabs, then you may create a bigger problem than you have now.

Good Luck.
I pushed the stern up over the dunes and locked the rudders down to see if re-drilling was a possibility but the existing holes make that risky. I would end up with one big elongated hole. I replaced the cam on the port rudder casting and that helped a lot. Several weeks ago a "friend" had tried to twist it unlocked with a pair of pliers and so temper was lost out of the plastic. This allowed the port rudder to pretty much do what it pleased. I'd still like to find a set of adjustable rudder castings though.