Easiest way to find a leak around the rudder post is to remove rudder, block the top hole with your finger and suck on the other side with your mouth. You will know in seconds if that is the culprit.
To repair is just as easy, because generally there is very little structurally wrong, just a small leak. I usually get a trimming knife and lightly cut around the outside of the post, 1-2mm wide and about the same deep V shaped just to get a round dam around the post. Fill the cavity you have scored out with a suitable epoxy, proper high quality stuff not you cheap quick set rubbish, it has to be very runny, it will wick into whatever small hairline crack that is there, a bit of heat will help the resin get a bit runnier, use a hair dryer. Once you are satisfied that enough has wicked in just stick a piece of plastic packing tape over the whole repair and turn the ski upright.
I a few hours remove the tape and you are done. Should not need any more finishing. I do it all the time.