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We don't allow Villain Sue. But to answer the main question: as long as the opinions are written properly I see no reason not to let both entries coexist.
YMMV is for general perception, not individual reactions. For both reactions to belong, each would need to have an observable camp in the fanbase, because otherwise, it's a single person writing that they disagree with the general fan opinion.
In the examples cited, I would rewrite the moment of awesome to put the character actually doing the awesome thing in front. Basically, awesome should be "X kicks Y's ass", not "Y gets his ass kicked". If it can't be written that way, it's probably not awesome. (I'm aware that there are times when a character surviving an ass-kicking against an overpowering foe can be awesome, but such an example also shouldn't be written "Y gets his ass-kicked.")
^^ Depends on the YMMV item. IIRC, Tear Jerker and Awesome Moments covers reactions of individual tropers and for the broader audience.
Edited by Adept
On occasion, there's things where the same situation gets put on opposing YMMV pages, along the lines of: Tear Jerker: "Alice dies" and then Awesome: "Alice finally dies". Since different opinions is what YMMV is for, and there are some characters who really are that polarizing, what's the right procedure to follow (if neither is particularly bashy)?
For example, there was a line on Isekai Quartet that said something like "Those who can't stand Ainz being a Villain Sue will enjoy seeing him finally get his ass kicked here".
Edited by Chabal2