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Your analysis seems pretty thorough. You have my vote. Since either translation is plausible, and there is no other context to go on...I would say the presumption should be in favor of consistency with the other occurrences of the word in DL. Since he is drawing from disparate sources, that weakens the argument, but what else do we have? Have you checked if any of the "festival" translators offer a justification for their choice?

I forgot the decisive factor: as a wise man, I tend to enjoy contemplation more than festivals. QED.

Based on this from Usener, it seems like DL's source is probably Epicurus' Problems, which he does cite as a source for another saying (per Don's website). With this additional context, I'm now leaning toward "festivals". (I'm assuming this is what the Bailey footnote referencing Bignone was referring to.) (Quote from Usener)

My take on the 2nd part of the Plutarch quote in U20: Epicurus' point was probably something like: most rulers would probably prefer to discuss military strategy and laugh at coarse humor. If that's the kind of dinner conversation that gives you pleasure, then that's the kind of conversation you should have. He's arguing for authenticity over pretense. That's pure speculation of course.

If anyone is interested, I found the Bignone text that Bailey refers to, but it's in Italian. https://archive.org/stream/epi…ooperefram00bari_djvu.txt Search for "1095" Here's a very rough Google translation of the Italian: (Quote) The Usener fragment he references is U386. It continues on...but I can't tell if his discussion of the shift in the text is related or not.