Isn't that worse? I don't see where you're going with this line of reasoning.
People fall for all kinds, shit there are people that love their partner even if they are physically and mentally abusive towards them.
Okay, but contrary to the popular saying, all is not fair in love and war. You don't get carte blanche to do whatever you want just because you're in love with someone. She knew that it was wrong to treat the kid the way that they did, but she did it anyway. She doesn't get to absolve herself of wrongdoing just because she did it for a guy she liked.
I've just checked the conversation there, it doesn't say she left him with no money when Katie asks him he stutters and the conversation gets changed.
All he says is she made it clear he wasn't welcome, that's a big difference than being thrown out. He could have gone back but it would have been awkward.
Did you also replay the part where she sends you an email?
Elaine: "Thanks for moving out without much fuss. I hope you understand it's for the best.
Elaine: " I Hope you found somewhere to stay..."
MC: "(Hmm, sounds like she is being nicer than usual....)"
Elaine: "But please don't think you can come back if you are having trouble finding somewhere.
Elaine: "I want to be very clear. This is no longer your home and you are not welcome here."
MC: "(Yep, that's the bitch I remember.)"
Elaine: "Please let me know your new address ASAP and I'll ship the rest of your stuff. I don't want it in my house."
Elaine: "If I don't hear from you in three days, I'll assume you don't want it and it will go in the trash."
MC: "(Fucking bitch)"
Then later in the game Bella shows up to deliver some of your things that she pulled out of the trash.
MC: "Hi Bella. What are you doing here?"
Bella: "I'm sorry, I didn't want to cause trouble. I eh... I have some of your stuff here. I noticed that Elaine had put it in the trash, and I... I felt bad for you, so I wanted to drop it off here, rather than let Elaine dump it."
MC: "She dumped it already? I was going to collect it tomorrow. What a fucking b.... eh... bad thing to do! I cannot believe she'd do that!"
Bella: "It's OK, you can call her a bitch. She's my sister, so I'm not going to badmouth her... but I understand it if you want to. I cannot defend what she did with you and your house... and now.. your stuff..."
So, I think him trying to return home would be more than just awkward.