My husband and I are escapees from the Rotten Apple. I grew up not too far from where Mr. Greenfield lives now. We were lucky to find each other: conservative, religious, both Alphas but I was happy to be the Beta to his Alpha in most things.
He grew up at the same time period we did; where the pressure was on to "score" as many times as possible (something my husband and I rejected). I have a feeling that Mr. Greenfield wasn't built that way, either, but nonetheless felt the pressure of it from friends and their exploits.
So he did what he thought he must to compete in an ultra-competitive meat market: he focused on being as successful as possible. Money is power and power is attractive. So while a part of him wants the "trophy" wife to show up all the friends who probably snickered at him over the years, what he truly wants is a loving, traditional wife who will give him kids.
Have you seen the young women nowadays? Hard to call them ladies.
A lady, who wants to please the man she is with, could rock Mr. Greenfield's world without ever hitting the sheets. She could make him feel like the action hero star of his own movie. A lot of young women today either lack the finesse to empower the men they are with, or are too selfish to even consider it! They would easily stick their nose up at a Mr. Greenfield, a smart, successful, religious man looking for marriage and to start a family, but hook up with some perpetually adolescent metrosexual who's "fun", and then cry when "Mr. Perfect" turns out to be "Mr. Selfish Jerk."
My brother devoted many years to building his empire. When he finally married at 46 year old, his wife was everything Mr. Greenfield was looking for: smart, beautiful, refined, happy to stay at home, a great sense of humor, with a Midas-sized bank account (and Jewish, too!).
He needs to come to Texas; we have some fine, beautiful Jewish ladies here that will put the stuffy New Yorkers to shame.
Now, there's nothing wrong in trying to get the whole 9 yards. The beautiful person, who is also sensitive, loving, perfect figure, super smart, respectful, great sense of humor, etc etc etc. It is just quite difficult to get all of that, and for most people two things are important. A) Ensuring that you have a priority list (eg a nice loving woman is wonderful, even if she doesn't have a perfect body and perfect hair), and B) looking at yourself and seeing whether you have what it takes to attract (and keep) the Amazon Princess you have specified.
If the guy wanted a nice woman who is beautiful (inside and outside) who is Jewish I don't think he'd have much of a problem getting her (unless he is a jerk), but he doesn't want that. He wants someone who looks like a super model, with a great sense of humor, very smart but not too independent and self driven, who is Jewish but doesn't live in an 'artsy' side of town. Does she exist? Maybe, but what does he have to offer this dream woman? Money? Not good enough, since a lot of the men who are members of the top echelon dating sites (see the ads in high money magazines like the Robb Report) are far richer than he claims to be (made his millions in an investment firm). If all he has to offer is money then, as the dating company execs told him, he is asking for women out of his league. If, however, he wants a good woman then he should stop using these dating platforms for rich men and pretty women (that have an interesting reputation btw) and simply do what you said. Leave NY, go to Texas, and if he is a nice guy he will not have any difficulty getting someone. She may not be a perfect ten, but she will make him exceedingly happy.