It's called stupidity. Any one of those could have given him a place to stay instead of Monica and completely messed up her plan.
Again, Elaine isn't stupid, far too much of that is left to chance and there is no way anyone would risk millions on chance.
What tracks do those mails cover exactly?
All the mails originated from the same place, if someone was trying to cover their tracks they would have sent those mails from different places. Sending them from only 1 place has only left 1 track, it's the worst attempt at a decoy ever.
I also think, we are not getting everything from Elaine as well.
If you remember, Elaine has two sets to her part.....1) To get the house...and 2) to get the money.
We know for her to get the house, she has to be as she was and be a complete bitch to the MC (that was the condition for the house part).
We also know that for the two Gold Diggers, their part for getting the money was going to be particularly hard for them.
I suspect, that Elaine's part (for the money) is to keep the MC away from Monica and her girls. Since she had already maintained a bitch stance up until now, it would be unlikely she would be able to accomplish that task. It is also the father's way to laughingly set it up, to where she has to make a choice between House or Money.
I think the other Gold Digger's part for her money, may be along the lines of getting the MC to go back to Monica and see that he stays.....something along those lines....to pit both Gold Diggers against each other.
Just some observations, I'm still enjoying the game and looking forward to more of the story unfolding...............Peace!!