I have to say I am surprised you can make it through this episode unscathed on the manwhore route. I really can’t wait for it to really blow up in the MCs face.
The only thing that bothered me was the random introduction of the beach house security team. Why if people need to be on the MC’s list to visit, have girls been able to come and go as they pleased. It felt very forced just to have an excuse as to why we couldn’t talk to Elaine
It's worse than you think. If you go back to one of he early chapters when Jenna is hacking Jolina's computer, you can clearly see Bella in Jolina's apartment.
Now suddenly at the end of the update, you can have it be that both of them are living there and act like they're fighting, but if you calm things down Jolina will call Bella 'hun' and Bella lets the "Jojo" nickname slip as well. Which is way too familiar for two women who were just being really bitchy to each other. In other playthroughs, if you aren't with Jolina, she'll mention she tends to only date women, not many men.
So here's what I think the true situation is:
1. Elaine has to get her will condition to get the money.
2. Elaine really has cared about you all these years.
3. Elaine knows about your will condition and also knows you'd never do it. She brought you back into Monica and the girl's lives to ensure you wouldn't make that choice.
4. My personal conjecture is that she intends for you have your cake and eat it too. She gets the house and the money, gives you part of the money which the will can't stop her from doing.
As for Bella:
1. I believe that her and Jolina are still together.
2. Bella's will condition has something to do with either causing a fight between you and Elaine or making sure the two of you don't fulfill your will conditions.
3. Bella acts like your ally while at the same time was probably the convincing force behind Elaine sending the emails and tells her where to send them from (where Jo is complicit).
4. Jo is going along with all this because Bella has told her it will provide the money to make up for her losses from the coffee shop or that she will be able to keep the shop going.
5. Now that Elaine is so close to completing her will condition, Bella drives over to you to convince you Elaine has been evil from the start.