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Mark _australia said..
As an aside, who made the tool to re-cut the seat (Imax was it you?)
I want one as I visually check the vent on all boards I make but to just use a tool to ensure its good angle, flat etc would be nice insurance.
I always re seat all holes I come across

I use a drill bit , ( 14 mm from memory ) , that I resharpened to give a slight angle and a radius on the ends ..About halfway between a normal drill angle and flat . The trick is grind the lead angle so slightly that it doesn't grab the plastic and just slightly shave off a ****teenth . Twisting the drill bit by hand , never in a drill.
None of mine have ever leaked , but I'm a non unscrewer , apart from the odd occasion , like in a board bag on roof racks in the blistering sun . I believe a lot of leaking is because of unscrewing . Sand gets in and shreds the o ring and the seat . When an o ring gets sad , it pushes sideways and splits and breaks . My advice to unscrewers is to replace the o ring regularly . They get hard and flatten quickly . As said above , it only coasts a couple dollars for a handful . Id also suggest getting the next size up in cross section .
I personally wouldn't use grease on the o ring , it will attract sand .
Creating this kind of action instead of flat . My theory is , it stops the o ring squashing out sideways .