Rudder repair questions

[TitanTn]

I'm fairly positive my rudder was leaking this past summer. I would consistently get water in my bilge (although not a consistent amount). I checked every other way water could be entering and it has to be the rudder. So I dropped it out tonight. I think I found the cause of my leak. But I have at least two questions:

1. Should I pull the base plate off and re-bed it? I don't THINK it was leaking around the base.
2. You see the pitting on rudder? Anything to be concerned about?

Thanks.

http://unumemarketing.com/boat/rudder.jpg

[TitanTn]

Okay, I've made a little progress. Well, not really. I'm definitely going to remove the stuffing box since the bedding is looking tired and the bottom of the bolts are as well. It'll be good to know this is re-bedded well.

On the other hand, I called skidim.com and they confirmed that my particular rudder box was only made for a short time and there are no parts for it. I'm going to go to Napa Auto Parts and try to match the seal up, but I'm not holding my breath. My only other option is to replace the whole rudder assembly. Can anyone help me out there? Recommendations?