I removed the coolant transfer pipe (smaller one) by turning and pulling, greased the new with rubber grease and, with the help of a borescope, managed to get the new pipe in. It felt like it made a solid / rubbery o-ringy feeling connection... I twisted it a bit to make sure and it felt ok, not loose at least. Now I've fully reassembled it and driven it for 20mins or so and no leaks, I'm willing to call that a win.
Checking the history those seals were all last replaced in 2018, apparently, for the previous owner when doing the intake gaskets. (It doesn't make sense why they'd change these, but hey)
But... the water pump seal for this pipe was completely rooted, so much so that the new pipe would have been totally loose in it. Lucky I had a new pump and seals...
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