Still the most interesting thing for me is how she or any of her team found out about MC's conditions so they decided to set him up even before he had any idea what was about to happen.
If Elaine did try to set the MC up before finding out about his will conditions then she is officially the dumbest person in the game.
Not only did the same mail get sent to several of his friends, they had no way of knowing Monica would be able to take him in.
So not only could one of his friends ruin their "plan" but it had no clear goal.
That would have left everything up to chance and with that much money on the line it would be dumb as all hell relying on luck.
Not only that but she also gave him the beach house meaning he has another place to stay to fulfil his will conditions.
Not only that but she's also starting on a journey towards banging him which also helps towards his will conditions.
So if Elaine was behind the plan to set him up, she's done nothing but help him since thus marking her as the official numb nuts of WTHI.
The only way to set the MC up is to keep him at Monica's which Elaine, Bella and Jolina are doing a really bad job of. Bella and Jolina are both after him moving out into the beach house and Elaine has enough room for him to stay there if they get together.
Even if Elaine has conditions that require her to be near the MC that too helps him with his so he wins either way.
tl;dr Bella, Jolina and Elaine are all helping him win his money by doing what they are doing. All of them will end with him leaving Monica's which is his will conditions met.