Graham, I'm starting to see a bit of an ego in you. You've built yourself into something bigger than you are IRL, I think. I know lots of 27 year olds with great jobs and lots of money, women included....maybe it's just the circles I run in. You keep comparing yourself to everyone else your age and then declaring your superiority. I think it's your inner fat kid talking. You were used to being ridiculed and now you want to turn it around on the world and say "In your face!" It actually winds up making you look arrogant. Women with brains and money don't put up with that shit. Honestly.
You get what you deserve; and if you're subconciously putting out a judgemental, materialistic attitude, you're going to attract women that fit that attitude.
Live as if you were to die tomorrow. Learn as if you were to live forever. - Mohandas Gandhi