Tomfoolery wrote:I haven't done this, so take it all with a grain of salt.
I don't think I'd want to grind that glass, in large part because of the dust that's almost impossible to get cleaned out without wearing it. But you might want to consider either glassing the tube with the proper fabric and resin, or drilling it out and installing a proper thru-hull. I'd use a wooden dowel or slug turned on a lathe to center the hole saw.
You might be able to make a form that can be bolted thru the hole to make a flat surface on the inside using glass and resin - you only need enough thickness to make a flat surface. Basically glass it, then clamp the form with a center bolt through the hole with some sort of release agent (wax paper?) so the inside block doesn't stick to the partially cured resin.
Just some random ideas, which may or may not be useful. But it's the first thing I thought of.

Thanks for the reply Tom. I don't think its worth the trouble trying to seal up what is already there. It looks like its been done at least once already, and failed (apparently). So drilling out the old pipe and installing a proper thru-hull seems like the best way.
But I hear ya. Grinding it out perfectly flat would be a bear. And I hate working with fiberglass resin.
My Hunter had plywood backing plates for all its thru hulls. The plywood was shaped to the curvature of the hull on one side to give a solid flat surface on the other.
What about this idea... with a dremel tool I can probably cut away the largest resin "gobs" that dripped down the wall at the bottom of the pipe ( I really need to get a pic posted of the situation just to show you how truly ugly it is). Then fabricate a plywood backing plate and shape it a bit to take care of some more of the irregularity that surrounds the pipe hole. The transoms rear wall is pretty flat in this area, its the excess resin that was applied that is causing the irregularity. Then assemble it all together with 3M 4200 sealant and generous sealant applied between the inner hull and the wooden backing plate.
It is the interface between the outer mushroom head and the outer hull surface that provided the seal, correct? I think I could provide a solid flat backing for a thru-hull by doing the above.
Please all.... feel free to poke holes in this (pun intended).
Other facts I want to include in the post for the sake of completeness.
The OEM hose is clear vinyl, not black. The black color it takes on is just from interior sediment, dirt, or mold.
I still have not seen any signs that the OEM plastic 90s are barbed. I did however find two stubby 1" nylon elbows at West marine to use as replacements. I also bought 3 feet of Shields 1" reinforced vinyl hose.