Women will always be hypergamous. Self esteem typically plays a role in what type of partner you can get, and women typically have lower self esteem than men, but they still typically have higher standards than men.

When it comes to short term dating / hooking up, men typically have to settle for whatever they can get. If you want casual sex with 5/10+ women on a somewhat regular basis, you pretty much have to be an 8/10+, possibly 7/10 if you're lucky, chad. It's the opposite for dating / long term dating. Women typically have to settle for what they can get, while men try to get the best woman they can get. So ideally, the man and the woman get their looksmatch, ignoring things like one partner potentially having a disgustingly large amount of money.

For short term dating / hooking up, looks is pretty much all that matters. As a man, you'll work towards maximizing your looks, getting lean and jacked. For dating / long term dating, not being mentally ill and having money matter way more. The neurotypical man with a lot of wealth is going to have way more success here, and the broke and mentally ill man is going to have the least. Both short term and long term dating are unfair, but I believe it's easier for men to improve on their looks to achieve 7/10+ looks than it is to drastically improve on mental illness and become wealthy. It's easier for the average man to improve his short term dating success than it is for the average man to improve his long term dating success.

If you read any of what OP said, you lost the game.