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Replacing Drain Tube (Bulkhead)

Hi. So I'm looking at these drain tubes in my transom. I want to replace them both because they were definitely leaking into the transom. I'm not sure what they are called. The one for the splashwell (top) is this cheesy plastic thing and looks easy enough to replace and seal. But the bottom one was brass and it was a bit of a bitch to get out. She was tight. It think it was tapered and I'm guessing it was pressed in when the boat was made.

Here's my questions:
1.) What are these fittings called?

2.) For the bottom one - I would like for it to seal against the transom in both the inside and outside of the boat. The outside for obvious reasons, and the inside so water that sits in the bottom of the sump (there is always a little bit that the pump can't get to) doesn't get into the transom. I was thinking a threaded bulkhead style one. Is that an accepted drain style for that part of the boat? I wonder if I would be able to find one that would also still fit that rubber plug?

3.) If it really should be the tapered brass type. How do these work as far as installing goes?

Thanks!
 

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2.) For the bottom one - I would like for it to seal against the transom in both the inside and outside of the boat. The outside for obvious reasons, and the inside so water that sits in the bottom of the sump (there is always a little bit that the pump can't get to) doesn't get into the transom. I was thinking a threaded bulkhead style one. Is that an accepted drain style for that part of the boat? I wonder if I would be able to find one that would also still fit that rubber plug?
Ayuh,..... You'll be way ahead to just butter up the insides of the hole to seal up the wood, 'n screw on a screw-in garboard plug flange on the outside, like most higher end hulls use,....
 
Threaded with a flanged nut would certainly be easier to install but may have trouble finding the correct length.. Would just cake the crap out of it with 5200 and crank it down. I've seen the long brass tubes on whalers and believe they require a flaring tool similar to making brake lines for a car. It is a really pain in the ass if you have limited space to work with.
 
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