I'm in the process of replacing my first thru-hull. The summary, so far, is
here.
The part of your posting that would worry me is this (I cut these pictures down a little in size):
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Maybe there's a recessed head on the thru-hull or maybe you have something I ran into:
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This was under the static water line so I was glad at least there was a valve there. Yours appear to be just above so that's up to you how you would handle it.
What concerns me is what I found. The flange base for mine was buried in the hull layup. The hull thickness at the flange is only about 3/8 inches versus about a 5/8 or 3/4 inch thick hull for the surrounding area. (Can't really tell because of the grinding I did to get the old one free.) What was worse, there was no thru-hull "head" (mushroom or recessed) there. Instead I found a plastic sleeve embedded in the hull. You can see it as a shadow in the first picture and it was visible once I sanded off the bottom paint. The 2nd picture shows what was left of the sleeve when I finally got it out. The rest was shavings all over the ground.
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I'm not an old hand at this but I would be concerned if there wasn't even a bronze or Marelon thru-hull installed underneath those piles of fiberglass/epoxy. What I ended up with, after getting the plastic out, was a big hole 1/4" wider than the thru-hull fitting. A gap I'm going to have to fill in to get a proper seal.
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Someone else mentioned the concern of the corrugated hose connected from the bilge pump. This is easily cut or broken off even when new. It may be above the waterline now but in choppy water or a big sea, they may not be.
Just some of my thoughts.
ETA: The rudder post appears to have a stuffing box so there must have been some concern by the builder of water ingress at a point higher than those other thru-hulls.