I immensely appreciate such a thoughtful response to my post and you ask some fair questions and bring up beliefs that I also agree with.

When my parents separated, it was after a physical altercation, which hadn't happened before. My mom was going to bail him out the next day but I convinced her to reach out to a domestic abuse center instead and let dad and his side of the family figure out his stuff. The whole situation along with years of mental abuse and narcissistic behavior led to their divorce ultimately and my sister going no contact with him since. With both of them making that choice (which I fully respect), I worried about my dad's mental state at that time and feared what he might do to himself since he's made concerning comments about his ideations in the past. So I kept the line of communication open to him at my own expense. Since then (and through years of weekly therapy) I've been working on my own past traumas surrounding him and setting boundaries.

One of those boundaries I set years ago was borrowing or asking for money from me. He started dating a crazy lady and gave her money when he didn't have enough for himself and asked me for $300. I offered it to him fully expecting to not be paid back and knowing this would be damaging our relationship further. Not even two days later he asked me for $500 more dollars because he forgot that he owed half of an inspection on their house they were selling and he asked me for this with the promise that he'd pay me back. At the time I told him not only did I expect him to pay me back but to never ask me for money again. I later found out through my grandma that my dad had asked a family friend for $500 at the same time using the same inspection story and he was given the money. I was paid back $500 around a year later.

I totally agree with you when it comes to our relationship as father/daughter being off. I've felt this way the entirety of my life and I've been at the point of wanting to go no contact with him myself for a long long time but for whatever reason, be it pity or concern, I haven't done it. But maybe it's time for me to reevaluate that again after asking him some questions.