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Air bleed holes in heads

Is drilling the heads for air release something that could be done with them
installed in a running car, as opposed to something only done with heads off?

I imagined drill shavings and thread-tapping shavings could easily be
an issue. But I intend to replace my radiator this Winter, so having
shavings lodge in this current radiator is not really an issue. And I
also currently have a Tefba coolant filter in place; its purpose being
to trap any free flowing trash prior to the new radiator install.

I'm thinking now would be a good time to get those air bleed holes
installed in my engine?

Larry
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