The game makes everything possible to make you hate Elaine but... i guess it's too obvious to be the reality.
In the opposite the game tend to push you towards Bella but in the same time it gives you hints on who Bella really is.
She shows up with your stuff accusing her sister to have trown it out then later you learn that there is a little problem with this as Elaine sens you a message about it and the time doesn't match. Then Bella is clearly spying on her sister and betray her even if Elaine has taken her witrh her in her house. And about this, don't you find strange that Bella lost her so said job and appartment just as you dad died, did he paid for her so was she the second gold digger ? It would match perfectly with your asshole of a dad to take the two sisters and then making them do bad things to be able to keep the money.
I would guess that Elaine had to throw you out but was worried about you and found a way to make sure you meet Monica and Bella had another goal, maybe she has to seduce you to fullfill the will!
And last about that will, i guess that it's the last test you dad made for you. He thinks that you're a lazy fuck and that you will take the opportunity to get the money and live like a lazy fuck on his money. But i guess that he secretely wants you to refuse it and be a man and make your own life and money just like he did. That's why he tries to push you to your limit, to make you his bitch, to make you do horrible things for just beeing able to not have to make your own life. Then he will win, he will prove that you are just an asshole, ready to anything just to get your regular payment from the trust, you will be his puppet even after his death!
So be a man give him the finger and go piss on his grave, the fuck with the money, you can make your own and have your pride, that's the only thing that really counts!