Turned down two potential partners whose company I enjoyed immensely because the first one (ivy league degrees, spoke 4 languages, virtuoso musician) could not hold a job for more than a couple months and had zero life-savings and the second one (beautiful, charming, popular) turned out to be a narcissist that was over $1M in the hole due to the housing crash. Both had expensive tastes despite this.

So yes, if I found out the receptionist was falling ever deeper into debt and/or wasn't doing something on her own to rise above the seemingly unstoppable ongoing wealth redistribution to the top 5%, I would not marry her. OTOH if I found out she was a diamond in the rough like I alluded to above, I wouldn't let her out of my sight.

Fights over money are marriage-killers. And to quote Faye Valentine: "Beautiful skin can only be maintained by tireless efforts which are ultimately totally futile." So what's in it for me in this case other than transient enjoyment followed by a lifetime of sorrow?

Then you marry them.

And get divorced a few years later once both of you realize that "enjoying each others company immensely" is not sufficient to have a successful marriage.

He seems to be implying that, from his past experiences, a certain degree of mesh between their relative financial security and personal aspirations is a prerequisite for lasting "enjoys each other's company".

You may as well ask why he would not marry somebody he is not physically attracted to.

Then spend a lot of time together.