should i use the hobie drilling guide for the bottom hole to make sure its in the right place? and then drill the top on further back right?
If both holes are wallowed out, which they probably are, fill both. Grind a little keyway in the old hole with a Dremel so the epoxy will get maximum grip. Clamp the rudder into place in the lower casting mounted on the jig with gudgeons. Set the rake that you want, and the rudder all the way forward in the lower casting. You will still be able to see where the old hole was, so use that to sight it to level in the lower casting before marking the new hole location. Mark the hole center with the brad point bit, and drill it on a drill press. Don't use a pencil or pen to mark to try to mark the center of the hole. There are no short cuts to getting it just right. Don't drill the holes without a drill press. Shim any slop side to side while you're doing it to, and get new cams before you start.