Your inferences regarding myself seem to mimick your incompetance regarding the female persuasion, I'm not surprised.
Not that it really makes any difference, you should be able to spot good advice from any source, but to validate. I'm in my early-mid twenties and have a dynamic job in real estate development. I drive a nice car, have a nice place, and even work with WOMEN as you call them. Many are of the quality you speak of, and would kill to get it on with a hungry young entreprenuer.
I have never 'dated' a woman who has approached me. Why? Because there isn't a challenge, these types are generally the clingy, possessive 'i need a man' types from my experience. They are looking for wishy washy guys who don't have the cohones to become masters of their domain. I have little to no use for these women, beyond the free sex, I'm sure you would come to the same conclusion.
You seem very content to limit yourself to the stock of woman who make it convenient for you. And then whine about it. Becoming more and more stable as you age has nothing to do with becoming content. Hunger and passion drive our lives, and is the lifeblood of our souls. Women are attracted to this. They do not want to equate the term 'stable' with 'boring'.
So in conclusion:
I think you should read some pook and try to fire up the torch inside of you to go out, try new things, new experiences, new woman (perhaps gauge them on a scale more intricate than 1-10 on looks) And enjoy meeting them, failing with them, loving them, and living your life a little fuller than you did the day before.
This is what I'm doing, and since you "more MAN than me on your worst day" it would probably help you out. You seem like your in a rut. Become a man of action to get out of it....
Goodluck
p.s. "Spank Nuggs" ????? Well, I guess your still working on your creativity.
And for the record, YES, you do walk for "punanny" as you call it while I run. Thats why I'm ahead of you....When you're 50 and worn all the skin off of your right palm, you realize how far being a WISEASS got you....