Who, in the world, wrote that first "Trivia" entry?
It's been speculated by most game boards
that the mysterious e-mails from "A friend" are actually sent by Grout,
This is a really, off-the-wall suggestion. I can't wait to hear the reasons...
While the fledgling finds a staked skeleton in his mansion, it's shown in game that vampires just turn to dust when they die.
What has this got to do with Grout writing those emails?
It also explains why a disguised Ming Xiao is so distraught when she leaves
How does Grout sending these emails explain her "disraught"?
The e-mails are also sent by somebody who has to have some form of precognition,
Oh, you mean no one else in the game knew what was going on behind the curtain?
the audio logs he leaves are placed conveniently where the fledgling may find them
Not sure what this has to do with the emails, but are you sure this isn't just a game design decision?
he must have known they'd have been destroyed in the fire
Can you prove that he knew his house would be burnt down? It did catch fire after he died, and it wasn't started by his murderer.
the E-mails are mostly chess references, which rule out Jack
I'm not sure I follow this logic. Are you saying that referrring to the whole charade as a game is outside of Jack's character? I don't think they were sent by Jack, either, but I think he's a better contender than Grout. Grout cared little about other vampires, why would he call the Fledgling his "friend"?
his mansion has a checkerboard tiling
Now, you're grabbing at straws.
All right, grab a seat. I'll tell you who is (probably) really sending those emails. The Cab Driver (aka Caine). Working directly with Jack, and Jack saying "It worked just like you said", we can assume that Caine was pulling strings throughout the entire plot. Therefore, he wouldn't even need Malkavian voices to tell him the future to know what was going on. Also, if you talk to Rosa with a high persuassion level, you get an option that gets you a response like this: "The winner keeps his hand on the pawn". You never personally meet Grout. Grout doesn't even aknowledge the fledgling's existence. Jack does however. Jack helps you throughout the game, so ruling him out because 'chess references', is completely asinine. Caine, being the cab driver, is around the fledgling even more than Jack and works with Jack throughout the game. Maybe he's "keeping his hand on the pawn"? On top of that, the ominous tone of the emails fits his speech style perfectly.
I think that trivia blip should be removed. It's a completely off-handed concept, presented in a very messy way with absolutely no logic.