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And I figured it’s because they’ve committed themselves to an -on-Rails solution.
Python = fixed space syntax = I won’t ever consider it a modern language, even if so many people like it.
I think the very modern way to build a highly customized booru like Derpibooru is node.js + tons of server-side Javascript. Yeah, hardcore.
It’s a matter of specific characteristics and personal preference. Maybe something about Ruby is exactly what a booru needs, and/or maybe Clover simply likes Ruby. That’s why.