I may have solved the issue, but thanks for the input.
I found some pulleys at the hardware store that can flat mount to to a piece of wood via the back of the pulley bracket. I put new wire rope, bought a crimping tool and nicro pressed the thimbles in instead of using the bulldog clamps just to make it a bit cleaner of an install.
I tension the system with turnbuckles aft connecting the lines to the rudder shaft.
This fix cost me $80 including a bunch of spare wire rope, hardware store pulleys, Nicro press crimp tool and other hardware.
I am currently searching for higher quality stainless steel pins to replace the questionable ones that came standard with the pulleys.
Hopefully it is fixed for good now, but I will not know until I have a few hundred more miles under my keel with the improved system. I was only having issues in one specific spot every time something went wrong, so at least the issue was consistent. Hopefully these cheap hardware store pulleys are up for the job, if not I will have to make my own blocks as I refuse to pay $30 for something I would need to modify to get to work anyway. If I eliminated the abrasion that was occurring, I think I should be in good shape. Only time will tell, and I have plenty of spares.
I have moved on to the next stage of my junk rig conversion, enlarging the rudder and sorting out the details of the self steering and aux rudders.
I am debating building an entirely new rudder and using a new rudder shaft, but that is more work and more money. I would like to just enlarge my stock rudder a bit. Any input on how to go about that? Arne suggested just gluing plywood to the sides to increase the length of my trailing edge. I think this would be the easiest and cheapest way, but def the least posh. Not that it matters, It's not like my boat is some bristol yacht. I am considering attaching foam to the trailing edge of the rudder, working it to shape, and putting a few layers of grp cloth on it. I am thinking if I go this route I will use 3 maybe 4 at most layers of fiberglass to allow it to crush and avoid damage to the original section of the rudder if I grounded hard, hit a dead head etc. Any input?
I am in the design stage for my windvane self steering too! I am working from Bill Belcher's book. I am unable to mount the aux rudder on the centerline because my outboard is there, and I do not want to move it because I am afraid of messing with the boats balance. 25hp 4 stoke hanging off the back weighs enough to affect the trim if it is offset, my guess anyway. I am going to go with a horizontal windvane controlling 2 balanced aux rudders on either side of the outboard. Each rudder will be 1/4 the area of the main rudder. I am still hashing out the details, but I am getting together workable plan. Not having trim tab or bearings below the water line is a plus, aswell as being able to make the aux rudders flip up incase they hit something, or I need to reverse out of a slip, unfoul them ect.
The engage/ disengage needs the math finished, but I plan to make redwood, rock maple, or oak (ideally iron wood if I can find some cheap) rack and pinion gear system. The rack will connect the two aux rudders, and I will build a spring loaded engagement system to drive it. Pull a line, and the spring compresses and disengages the pinion gear, release it and it engages. Simple enough. I just need to find some nice quality old growth hardwood to build the drive gears from. I will varnish the gears and most likely keep them lubed up with healthy amounts of crisco or similar to quiet them down and help keep them from wearing. I am sure I will have some experimenting to do.
I feel it is prudent to take care of the rudder work and self steering while I still have the rig I am used to, so I can get it to work dependably. I do not want to run out of rudder when I do the junk rig conversion. Let me know what you think! Your input is always appreciated.