OK, I'm like 600 post from the end, so forgive me if this discussed then.
The most important thing to remember when talking about the will is that you can't be sure of ANYTHING unless you see it yourself. If you hear about it from someone, it could be a lie. If you see it for yourself, you know it's true.
Having said that, I am going to suggest a theory that involves things that two people have told you. I hope that this will lead you to believe that Elaine did not know the conditions of the will before meeting with the lawyer.
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Otherwise, Elaine did not know the MC's condition. So she kicked him out of the house and did not send the e-mail pretending to be the MC to Monica or anyone. When she found out about the will, naturally she had to change direction. Or, maybe the third beneficiary sent a bunch of e-mails, and a text message pretending to be Elaine, and has been lying through her teeth ever since. I don't KNOW who that it, but I suggest it might be Bella.
Some of this has surely been stolen from thing others have said RantingOldMan certainly having been one.
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I took The Don's "If Elaine knew she would have murdered me" as a reference to Bella. To me if Elaine found out that Dickhead Don had been "dicking" Bella that would have resulted in the most extreme reaction. Anyone else and she would have walked away (since she isn't into sharing) but her sister having an affair with her "man" would have been the ultimate betrayal. That's just my opinion.
As for the email, what if Bella and Jolina tricked Elaine to show up at the coffee shop? This is a super elaborate idea so most likely didn't happen at all but... What if they catfished Elaine? Elaine goes to meet her new "friend" at the coffee shop and is publicly humiliated... Thus Elaine refuses to go to that coffee shop afterwards, Jolina has footage of Elaine going into the store around the time they sent the emails, and I told you this was way too complicated to be real...
As to the conditions, I think that the second Gold Digger is the one who knows everything. If the second gold digger is Bella then perhaps she was little dick Don's real "partner" in that she was just as manipulative and evil as he was... To get all the money she needs to ensure that the other two don't fulfill their conditions so she sent the email and is trying to shove a wedge between the MC and Elaine.
I'm worried about how elaborate the ending of this game will be; I don't want it to be "realistic", rather I want it to be logical within the world that the story has created. We shall see if they can pull this off, I hope so.