So he doesn’t want to see a therapist for better communication but he can’t communicate “hey, I need to deposit $300 to my family at the end of the month”

How is she suppose to know your family depends on you financially if you can’t talk to her about it. Plus, how willingly would anyone send money to STRANGERS? (Because he’s never really introduced her to his kids and other important people).

They need therapy. He need therapy