I had a crack on the leading edge of my rudder on my CS27 a few years ago. It was between the lower and upper gudgeons with some below the waterline and some above. My rudder is outboard so it was fairly easy to remove and bring home for the winter to repair... I don't think the Catalinas are outboard mounted so yours may be tougher to remove.
Anyway, I ground out the crack and made a bevel using an aggressive sanding disc and then applied progressively wider layers of glass mat over the area to fill the bevel and then overlap int the sound area of the rudder. I faired it in and applied Interprotect 2000 to it and then gel coat to the portion above the waterline. It has worked well for a couple of seasons under some tough conditions. You'll need to lightly sand off all of the bottom
paint wherever you plan to adhere fibreglass. Take it down to the just a hair below the gelcoat.
I agree with US27 above to drill some drainholes in the bottom of the rudder to let all water out. The inside of my rudder was bone dry when I did the work but it sat in a dry and warm house for four months over the winter before I made my repairs.
Good luck.