Your hatred/fear of rejection is constantly reinforcing the idea in your head that becoming even better than you are now is going to spare you from that rejection. More money, better wardrobe, better body, etc. = less odds of being rejected.
Now, this mentality is often very true, particularly for men who go through the process of some significant self improvement. Going from a chubby kid to having a rock hard beach bod is going to make a big difference in how women see you, and it does in fact often lead to less rejection.
However, there is a point in which you are going to plateau, and if all of the things you say about yourself are true, then you have already reached that point. From this point on, the next improvement above what you already possess will have to be a fairly big leap to see a noticeable difference with women.
If you are currently making ballpark $200K/yr, making $300K/yr. is not going to lead to any significant changes in your situation with women. You have to jump up into the $1,000,000+ bracket to see the next level of significant change in how women react based on that particular facet about you.
If you are already fit, lean, muscular and looking great on the beach, knocking off 2% more body fat or adding another inch to your biceps is not going to lead to any significant changes in your situation with women. You basically have to go Schwarzenegger to see the next level of noticeable change in how women who are attracted to that particular trait will react in new ways that they didn't before.
You want to step up to the next level or wardrobe from $200 Bugatchi shirts? You're going to have to start wearing $5000 suits to turn the heads of fashionista ladies away from the Bugatchi wearing guys.
After that plateau point, you have to go much bigger then you ever did before to keep the idea valid that more self improvement will lead to less rejection.
HOWEVER, you're already situated to the extent that you do not need to make these leaps to attract a good woman. You need to abandon all thoughts to that regard. You do not need to be a millionaire to find a good woman. You do not need to wear a $5000 suit to attract a good woman. The idea that you have to better yourself is no longer going to work for you the way it did before. It will not lead to results unless you make those massive leaps, which are unnecessary.
What you are looking for, and the way you are trying to go about finding it, is now the only problem you have. Nothing else. Just this.
You need to change the way you socialize with women that often results in rejection to begin with.
You often say that you find the women you're interested in to be in situations where it seems impossible for you to approach.
It is not the situation that makes it impossible. It is your approach that forces it to be that way. In your mind, approaching a woman is the explicit act of expressing your sexual interest in her. When a woman is surrounded by her friends and is simply socializing, injecting yourself into that general context with a sexual request is what often draws rejection. You end up being like a telemarketer who calls people during dinner time to request "a few minutes of their time" so you can try to sell them a tropical vacation.
People do not hang up the phone on these telemarketers because they don't like tropical vacations, Dave. They hang up because the approach sucks and it's annoying.
You are the tropical vacation.
The women in their impossible situations are having their dinner.
Your approach is the telemarketers phone call.
This is largely why you are not getting "a few minutes of their time" so that you can reveal all of the good qualities that you claim to have but supposedly never get a chance to display.
If you want to open and start talking to women, all women, hot women, you need to learn how to draw all people around you into conversations.
Last weekend I ended up at a rooftop lounge with a plate and we hit the balcony area for a while. We were sitting there having drinks and talking about open relationships, whether they work or not, etc. A blonde came over and sat next to us at some point, minding her own business, and after a few minutes I looked at her and said, "We're sorry! This poor girl! She has to sit here and listen to us talk about all of this stuff!" .
"Oh no! I don't mind at all!" she said. From that point on she jumped right into the conversation with her own opinion. She had a British accent and that lead into another conversation about her visit to the States, what shes been doing during her visit, places she should check out, where she is staying.... She became part of the conversation for over 30 minutes.
You need to learn how to do that.