Various Artists Not Appearing - Think I'm following the rules

Plex Media Server Metadata & Adding Files
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I think this explains what you’re seeing:

  • The “Artist” view in Plex is actually “Album Artist.”
  • When viewing by “Genre, Artists, By Title,” it’s likely that the genres attached to the VA albums have not been attributed to the ‘Various Artists’ artist.

If you edit your “Various Artists” artist and look at the “Tags” page, is there anything in the “Genres” field? If not, the points above explain what you’re seeing. If you add, say, “Pop” to the VA Artist’s Genre field, then set the view to “Pop” “Artists” “By Title,” the VA artist should show up.
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There are some Requests in the Feature Suggestions forum regarding this. It’s included in this request for better tag support, but more specifically in this one.