I hear you. I've had ungrateful family members drive me broke. Compassion is doing the right thing, even when it's scary, or it hurts, or no one is watching, or when people around you misunderstand and demonize you, or they are just plain ungrateful and leave you holding the bag. I admire your willingness to continue grappling with it and finding your own answer.
Regarding women again, are you meeting enough of them? What's the scene like where you live? I don't know what it's like in NYC, but the social/dating scene in my current city just doesn't exist, and I'm watching some of my friends grapple with seriously heartbreaking loneliness.
I don't know what to tell them. I'm dating my high school sweetheart again, but we were broken up for several years, and many of the experiences I had with women during that time were quite traumatic. The rest of them were just not a good fit. I had completely given up on dating altogether, at least for a period of time, and only then did the love of my life find her way back to me. Despite years of extreme loneliness in new cities, I still consider myself lucky and wish I had some actionable advice I could tease from the situation. I've even experimented with building dating apps because this epidemic just scares the shit out of me.
I'm not in NYC sorry to give that impression. I was mentioning NYC as far as being densely populated, I'm in the midwest. Honestly I don't meet much women outside of work or the occasional girl I run into at a gym. I know the cliche saying "go join a club" meet girls that way. I could see that but it's also possible I like being alone too but yeah it just bothers me that my self-deemed value is whether or not I get laid.
The other problem too today is the fakeness of social media, filters on faces, photos looking like peopel go to beaches all the time/live extravagant lives.
Bars it's like a self-control issue, use drinking for courage then you get too f'd up.
In the midwest but we have a small "city" with "skyscrapers" that I wanted to go into and do photography at.