I've seen this be a problem with well-off female friends again and again.

It's always a status issue when I've seen it (the women sees herself as high status and she wants a high status man).

Wanting someone well-off (more than say a million or two) really limits your dates, and is a problematic selection filter (you're chasing the same guys everyone else is chasing which leads to horrible selection biases). Specifically the men that meet the filter often have negative learned traits if they have plenty of women chasing them.

> that I don’t have to financially support him

An excuse. Plenty of men don't worry about that issue when looking for a woman. Independence is a nice-to-have .

I often ask single friends what their must-haves are in a date. The replies always worry me. Then you see them successfully find someone that doesn't fit their requirements (maybe flexibility is a selection bias for successfully relationships?)

Why is it so hard to learn meta-skills?

I don't hang around with enough wealthy guys to notice any pattern in them. The women I'm talking with this pattern are high professional income levels rather than deeply wealthy (I don't hang with them either).

People have such strange wants - money does matter but there's many other traits that matter more.