Don't know if he'll be able to block Elaine, being with him while he made money she could have that money locked in a court case for years. I'm still following the games logic here, the MC's dad had his mother locked in a court battle for child support for years, she won it just before she died but still, Elaine would have learned something from the old bastard.
Only way would be to find her conditions and screw her over but even then i'm not sure. Could probably be a chance then again she isn't really a gold digger she was the mans lover for many years, she's only looking to get what she is entitled to.
I am sure we'll be able to screw over the third party whoever she may be.