...hate to say it, but I think the biggest issue here may be a bit of a disconnect with life itself and how you're interacting with it.
I'll put it this way...I'm a teacher making $50k at the moment who drives a Mustang and goes to Planet Fitness, lol. Hey man, I don't really have any trouble meeting or attracting women, and it's mostly due to modesty/comfort in myself and genuinely having fun with life and people. You can have all the money and success in the world, and all the expensive posessions in the universe, but if your persona doesn't click with all of that...well, then what you have is just a bunch of empty objects that don't really help to reflect your personality and who you are to those around you.
To prove a point...I've learned more about developing social skills and the ability to speak and interact with other people from teaching high school kids all day than I ever could have from anything on here, you know? You can flash money, "spin plates", and "game" all you want like the "experts" say to...or you can actually learn to be social, develop a persona, be a leader who's not afraid to put himself fully out there for others to see, learn how to match witts with any human being, and let the rest happen on its own while you happily coast on auto pilot just doing your thing from day to day without much going into it. You can't hide behind money and success and expect it to do the work that your personality and social skills need to. I think this might be some of your problem.