The problem isn't that improving password checkers is hard
It actually is kind of hard. There is no way to "calculate entropy" when you don't know how the password was generated in the first place. I could be using completely random ASCII generator and there is some chance that I will get the password "password", which regardless is not a good password. There were some papers at USENIX this year about password strength meters where they use machine learning to judge the strength of a password but, no, it is not exactly easy.
A case in point is computer science in Malaysia and the U.S. While American computer scientists are depicted as male hackers and geeks, computer science in Malaysia is deemed well-suited for women because it’s seen as theoretical (not physical) and it takes place almost exclusively in offices (thought to be woman-friendly spaces). In interviews with sociologist Vivian Lagesen, female computer science students in Malaysia reported taking up computing because they like computers and because they and their parents think the field has good job prospects. The students also referenced government efforts to promote economic development by training workers, both male and female, for the expanding information technology field. About half of Malaysian computer science degrees go to women.
But that can't be true, because that would be admitting that there are innate differences between the sexes and that's just not PC to talk about.
This is easily disproven by looking at countries like China, Iran and others where women make up close to 50% of computer science graduates. Whatever the problem is, it is not "innate".
"When people are least sure, they are often most dogmatic." -- John Kenneth Galbraith