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Maybe I've misunderstood pvg upthread but I assumed "'homebrew' has come to connote scrappy and hip" was about IT/tech because it doesn't have that connotation in the actual context of beer, at least to my knowledge.

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No, you had it right - e.g. https://en.wikipedia.org/wiki/Homebrew_Computer_Club which, as you say, is probably a borrowing from older tech nerd communities.

The "homebrew computer club" made their own computers. It wasn't about being scrappy or hip, but just a cooler way of saying "homemade"

You should probably check out the denotation of 'connotation'

You should probably check out "being a pedantic douche" -- oh wait, you already did.

So it's about being cool but not about being hip? What distinction are you trying to make?

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