Rudder looks good to me. I've always doubted whether the rudder can be completely encapsulated against water intrusion over the long term. But, yours looks fine.
Seems to be water weeping from the keel void on top of the rudder shoe. Pretty common. Difference of opinion as to what to do about it, if anything. Wouldn't bottle it up and prevent it from draining. Not sure if its getting in there, or getting out there.