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The saddest moment for Hololive would probably be a popular member like FBK or Marine, or hell, any member really, unexpectedly passing away in an accident.
So many iconic moments would become hard to look back on because they'd have to acknowledge the member who isn't there anymore, and there's no easy way to hush and graduate them like Holostars because of the massive audience they have.
For me, my saddest moment is probably gonna be when Ina graduates.
I should just fuck off back to sleep, posting shit like this is making me sad.