I was going through the list in my head and I couldn't think of one male friend with lifelong money problems who wasn't married. Not one. Maybe it keeps a guy away from a woman who spends 2 thousand a month on her looks, but the average professional woman is fairly happy with a man who is a good partner to her otherwise but just earns less, especially if what he's doing has other value. I make in the top 20% and have few issues dating musicians, teachers, carpenters, etc. All of the men I've been with were just as interested in my career and pasttimes as their own. It’s the ones who are afraid to lose control by me having too many purse strings that can be an issue.

The biggest problem with the patriarchy is that too many men are taught not to value a womens' career and pasttimes as much as their own. He's the star of the show and all is supposed to revolve around him. So too many (and some women do this) expect their mate to give up the pasttimes and skills that made them attractive, in order to raise a family, and then wonder why they aren't attractive anymore.

Would your friend find better options if the words ambitious and driven were replaced by educated and skilled, and perhaps if he were just as willing to date someone 10 years older as 10 younger? I noticed you said young and attractive rather nonchalantly. No one is saying to turn the idea of chemistry off, just open the net a bit wider, and remember the attractive slightly older lady in his building could be an option with upsides.