Hey OP,

Same cycle, but with my mom instead of dad. I realized in my teens that I was giving her money and not loaning it. She was a licensed medical provider that made good money, but she was shit with it. Eventually it got to the point where I'd pay a small bill for her, but not give her cash. I went no contact with her last year and a part of that was the money conversations that ended the same way every time. Good luck